I just finished a guest lecture about digital transformation. It’s a lofty topic and, as with most inspirational speeches, it’s filled with platitudes about thinking differently, new strategic paradigms, and macro trends shaping how people will find and buy wine. But for this speech, I wanted to do something very different: leave concrete examples of great vendors and companies that wineries could trust. Vendors I would ask my wife or my close friends to use because they have working technology, good value for their software and services, a customer-centric philosophy, but most of all, the utmost integrity. Here’s my presentation of the objective recommendations, with an appendix of some vendors' sales presentations. And below is the context for each vendor in the presentation.

Foundational Tools: DTC

The baseline for digital transformation starts with the website. But it doesn’t need to be overcomplicated. A website serves three core purposes: it represents your brand and helps customers buy or find information. Designing it should be central to those three goals, provided it is responsive and performs well across a wide range of internet speeds.

Website and E-Commerce: Stop Overthinking It

The ONLY Platforms That Matter:

Commerce7: Andrew Kamphuis has spent nearly two decades coding DTC software built exclusively to sell wine. It’s not perfect, but it’s sufficient for the category, especially if you’re an omnichannel winery (hospitality, ecommerce, club) focused on increasing sales across all three.

Offset: Like Commerce7, the team at Offset has been serving the industry for over a decade (although under different names). They are ideal for high-touch, elevated wineries and retailers that prioritize deep customer connections. They are focused on high-end aesthetics and allocated/mailing list, membership, and hybrid models.

Shopify Plus with Awtomic: The newest kid on the block is Shopify, the world’s fastest-growing e-commerce platform. Shopify is the top-tier choice if you are only selling online. Still, it has challenges supporting omni-channel sales (the way the wine industry wants it) because you need to combine an infinite number of plug-ins to replicate what either Commerce7 or Offset launches with out of the box. That being said, the BEST plug-in that powers the club (subscription) processes and more is Awtomic.

I know other niche platforms offer lower rates, niche features, or allow you to ship under their licenses, but if you are future-proofing your winery, only these three matter. Pick one. Don’t spend six months in committee meetings. Your website isn’t the Sistine Chapel; it’s a sales and marketing tool. Make it responsive, make it fast, make it convert.

Design Agencies: The Ones Who Get It

If you’re going to hire an agency, hire one that understands wine isn’t just widgets and that it covers the three critical channels (hospitality/tasting room, e-commerce, subscription/wine club). Here are some of my favorites (not at all a comprehensive list, and I’ll continue adding to it. I’m also considering building a list of agencies that I would never hire.

Wine Works: The OG of winery sites. They’ve built over 400 wine e-commerce projects. They know what converts.

Gorilion: Fast, modern, and focused on function over form, but that performance comes with incredible conversion benefits.

• General Studios: We truly appreciate the high design approach they are myopically focused on.

• VinAgency: Seeped in wine and led by one of our industry’s stars, Katherine Cole, they have an exceptional ability to build DTC-focused brands.

• Offset: One of the rare vendors that shows up in two categories. Offset brings a distinctive blend of tech, design, and strategy. Their client list skews high-end, and because they have an in-house brand studio and production team, their website builds almost always come with real brand-building and storytelling firepower.

Add-ons that Actually Add Value.

Signals: This is the kind of tool we need more of. It turns Commerce7 order data into actionable insights without requiring a data scientist. Simple installation, immediate value. It tells you who hasn’t reordered, who’s spending more, and who’s drifting away — no queries, no filters, answers. Also, if you want to understand AI + wine, Stephen Mok is one of the five top voices actually leading the charge for our industry.

Digimatic + Klaviyo: For email automation that doesn’t require a manual every time you want to send a campaign. This plug-in and tool are underrated, as they replace multiple tools (Red Chirp + other email platforms) with more functionality at a much better price.

Fulfillment: The Unsexy Essential

Wineshipping: They do one amazing thing: get wine from your warehouse to your customer’s door. I know they power over 1,000 brands, and it’s been great to see how they continue to push the envelope for innovation. Aside from their ACP (Awesome Consumer Portal), I’m a giant fan of their Omnichannel Delivery (both DTC and B2B), and their new On-Demand Fulfillment Model that allows wineries the best of both worlds.

The Strategic Layer

Egan Wine Consulting: Sometimes you need someone who’s been in the trenches to help you see the forest for the trees. Michelle Egan is in an elite group of experts who have managed over $50M of winery DTC sales. She is also in the rarified group of marketers who understand both traditional DTC sales and digital.

Performance Marketing: ROI or GTFO

Stop throwing money at Facebook and hoping for the best. Work with people who understand attribution:

• Big Thirst
• Premiere Cru
• Mongoose Media
• Coast Digital
• Twibi
• Good Things Done Right

They know the difference between vanity metrics and actual revenue. They can drive DTC or 3-Tier measurable performance marketing.

The B2B Stack

Blended Tech: Finally, a modern solution to production management. Blended is building a tech-forward system that helps wineries use their production data to drive both quality and profitability, not just compliance. Its adaptable workflows flex to each team's workflow, making day-to-day cellar management more straightforward, faster, and easier for everyone.

Provi: This will be one of the structural change agent platforms for B2B AlcBev. If you are not learning about it, how to leverage it, you are missing out on the future of B2B ordering.

VinoSmith: A truly cost-effective wholesale operations and industry-specific CRM tool for wine and spirits. And the cost makes it the smartest first step.

Salsify and Syndigo: Digital asset management if you are in major chains. This category is still problematic, but these tools are the leading choices (primarily because of the retailers that support them).

Epsilon: Retail media networks are coming to wine. If you are a brand with major chain distribution and you don’t know them, you should. If you are with Total Wine, Costco, and so many others, Epsilon should be on your speed dial.

Pour Now: Shameless self-promotion? Ok. But we’re solving the discovery problem at the point of purchase. We have over 250 brands that use our platform to help consumers find where to buy their wines at the retailer of their choice.

We believe in our platform so much that any brand can try any tier for FREE, and if you don’t find value in the paid version, you can downgrade and use our free version, which performs 500% better than any of the competition.

Email me if you want to give it a spin.

Technology doesn’t replace us, it reveals us. The tools are finally here that can help us be better at what we do best — making great wine and sharing it with people who appreciate it. But they’re just tools. They won’t fix a bad wine, poor branding, lack of customer centricity, or lack of process.

The genie is out of the bottle. The question isn’t whether to embrace digital tools and transformation; it’s how quickly you can adapt before your competitors do. Hopefully, by giving you a shortcut to the best tools, you can get there faster.

Any solutions or partners that I missed? LMK in the comments.

My last article was a rallying cry to wine software providers to do better, many of whom are struggling to deliver on basic promises — practicality, ease of use, and immediate value. Thanks to my time volunteering at wineries, I’ve become more vocal than ever in my writing and social media posts, as my patience for tools that don’t unlock value but instead add complexity and busywork for wineries already under pressure. Rather than offering support in one of the industry’s most challenging eras, some of these tools are actively hindering progress.

But from my last post came a silver lining: several software vendors reached out to share their progress and vision with me, and among them, a few are genuinely building something impressive. As a wine-tech software veteran, it’s imperative that I share the best solutions with you and why.

If you watched yesterday’s Silicon Valley DTC Report, you noticed I spotlighted Signals — not for grand promises of industry-wide disruption, but simply because it has a singular vision to solve a key problem in a time when wineries need more help than ever to sell wine.

The software addresses a straightforward problem: wineries often overlook critical customer interactions because data is cumbersome to access and analyze. Signals solves this by turning Commerce7 order data into actionable insights without complicated setups, help from IT, or the need for data analysts to manipulate the data.

After a simple installation, Signals immediately creates clear, segmented lists — customers who haven’t reordered, those quietly spending more, or others drifting away. I appreciate that it’s straightforward, effective, and refreshingly practical. We need more of this approach from wine industry software vendors.

Signals isn’t just another tool that creates more work. It’s actually a tool designed to replace mediocre analytics and, more importantly, enhance your sales and marketing efforts. It achieves this by reducing a winery’s workload through automatically generated insights, rather than adding to it by requiring endless queries and filters.

The company's founder, Stephen Mok, has been working diligently to introduce AI to the wine industry and is rapidly becoming an expert in AI-driven solutions for the sector. Drawing on his experience and exceptional product development skills, he interviewed and collaborated with several premier wineries and DTC experts like Miryam Chae to develop the platform before supercharging Signals by integrating generative AI to analyze a winery’s data and produce targeted, actionable marketing lists.

These lists, or “Signals,” empower wineries to easily engage customers through tailored communications — email, phone calls, texts, or even direct mail. Examples include lists of customers who are due for their next purchase based on past buying patterns, buyers who’ve previously enjoyed particular varietals but haven’t yet ordered new vintages, or club members who seem disengaged and might benefit from personalized outreach.

The result? Wineries can launch targeted campaigns quickly — usually within hours — capturing incremental revenue efficiently and without hassle.

There’s a free option to try before you buy, but most importantly, the best value I’ve ever seen for a winery software to date — a straightforward Pro subscription at $50/month (less if paid annually). If Signals’ automated segmentation platform can’t help you recoup $50 of increased sales per month, it means there’s something else wrong.

While Signals is very different from the competition of overpriced analytics tools, the ability to switch and receive the same (and better) analytics, along with Signals’ core offering of supercharged AI segmentation, is a no-brainer. I also appreciate that Stephen and his team are willing to truly reward early adopters with an incredibly amazing deal — a limited lifetime subscription at $999 for the first 100 customers. That’s cheaper than both competitors’ products at their lowest yearly subscription.

It’s also refreshing to see their transparent roadmap for upcoming features that are powerful and practical. Here’s what’s next from them —

• Smart integrations (Klaviyo, Mailchimp, GA4)
• Easier list-building methods
• And clear revenue attribution to campaigns.

Signals isn’t revolutionary (yet). It’s just an effective tool that reduces friction and increases revenue. In a world of overly ambitious tech promises, that alone is noteworthy.

Check it out:

https://www.getsignals.app

Commerce7 Install Link

It’s nice to see a software company that helps wineries at a great price to increase sales. Any winery on Commerce 7 that doesn't take a chance trying it out isn’t serious about DTC. As software is constantly evolving, I look forward to seeing how this platform continues to develop. For now, it truly delivers for the price.

In the future, I will preface all articles where I make non-biased, candid recommendations for winery software, along with my reasons, with the title 'No Swirl.' In my next article, I’ve decided to name the only three e-commerce platforms I recommend and explain why.

The wine industry is hungry for solutions to help us sell more wine. Many people are working hard to make businesses work with some of the worst headwinds we’ve ever faced. And so many people are thrashing to provide poor solutions or ridiculous or overly simplistic excuses about what is causing wine’s downturn. The actual answer is — it’s a complex combination of many things . . . and solving it will require a multitude of changes.

I recently had a challenging exchange with an MW I deeply respect. I was calling out a wine-tech company that got some new funding after a decade of languishing by waving around the new cat-fishing technique of adding the hottest tech trend into their pitch (in this case, it was “AI”). They have been building and promoting a recommendation engine, which is pure nonsense (an article on Transforming Wine is coming soon). Company notwithstanding, the problem is that because they had friends who worked on the project, this person did not like my tone about stating that this technology wouldn’t work for wine in the near term. As an expert, they KNOW that. I challenged them to ause it on their e-commerce site if it worked so well which abruptly ended the argument but exposed a terrible problem that vexes our industry. Because of the US wine industry’s hospitality-based kindness and interconnection, no one is willing to stand and objectively say that a particular solution is not a good choice for wine companies.

After that exchange, all I could think of was that we needed the rawness of the characters Jeffrey Dean Morgan plays in movies and TV shows. He’s often variations of the gritty straight shooter. Despite many of his characters having unsavory and frequently outright terrible character flaws as part of their origin story, he often metamorphoses into the antihero who minces no words in telling uncomfortable truths. He varies between crude, antagonistic, and contrarian, but cutting through the center of his banter is almost always the strong dose of reality the episode or movie needs to ensure the plot and protagonist find their way to success.

I’ve been working pro-bono with several wineries to help them with digital transformation. One of the things I’ve noticed that creates confusion and impedes our industry’s progress is that there is no safe place to find expert opinions or analysis of software or vendors for the wine industry. Because the industry is so tiny and interwoven, and our Northern CA culture drives most US wine businesses, everyone in the industry is reticent to speak out. A very small group of TRUE experts earn their living consulting, and they are reluctant to stand up and say, “That is a terrible solution.” They cannot because wineries have relationships with some vendors that barely serve them. Equally problematic is that expert practitioners working for large companies (Gallo, KJ, Constellation, etc) are encouraged not to take a controversial position that may reflect poorly on the organization.

Culturally, it’s hard for most of our industry’s thought leaders to deliver the hard introspection like Scott Galloway, who speaks about tech and universities and how they are failing students. READ THIS ARTICLE. But imagine more people like Scott sharing what is good and bad about our industry with a searing truth that illuminates and sanitizes. Fortunately, we have some brave souls, like our own wine thinker, who often speak uncomfortable truths to our industry. We need more of this from operators, not armchair quarterbacks who have never or barely sold or marketed a bottle of wine in their lives. Sadly we are overwhelmed with “thought leaders” whose whole identity is often about being the authorities about choosing which products they deem to be drinkable — and lamenting about inflated prices, the sins of marketing, the “Big Wine” boogeymen, navel gazing trying to define ‘fine wine,’ proclaiming the natural wine revolution, or a myriad of other positions that gives them a perverted endorphin rush for being wine gatekeepers. This is our echo chamber.

But it’s not just pointing the mirror inward at wineries but especially at the industry software and service providers. For example, too many great tech companies have unrealistic expectations that an ecosphere of developers will build apps to help put two pieces of software together via APIs to make it easier for wineries to do their jobs. Unfortunately, instead, there is a dearth of talent that can help. Also every system has idiosyncratic behaviors, wineries often must discover those challenges AFTER they bolt systems together. It is absurd that these not already well-documented by some of our best software companies. We as a software industry can, and should, do better.

I’ve observed firsthand how small wineries struggle with even the best-of-breed tech solution. I’ve watched them lose valuable time in data reconciliation, re-entry, and shipping or compliance adjustments. It often feels like a black hole of wasted time and energy. This is unacceptable. It is hurting our industry proclaiming our tech solutions make their jobs easier.

Similarly I have winery friends who’s tech setup reminiscent of the Winchester Mystery House — barely functional and tied together by ducktape and bubblegum, but any change in systems presents massive challenges because it’s not just the software that’s the issue; it’s the complex systems and outdated business practices deeply embedded in their operations.

But it is hard to find truth as an industry. Especially when there’s a group of talking head writers who have never sold or marketed a bottle of wine in their lives and are happy to regurgitate press releases or company propaganda as if it were fact. It confuses the industry more and creates FUD in the market. How do you pick the best vendor when a writer chirps how a tech company “helps wineries experience a growth of between 18% to a whopping 41%” without checking if it is true and understanding why.

This is important because, with honest roadmaps and calling balls and strikes for which tools to choose, the path to success is not only stymied by inadequate solutions but also the weight of managing their deficiencies, resulting in a higher total cost of ownership but also higher setup and switching costs. That’s why wineries stick with terrible solutions for years rather than switching. But it’s not as plug-and-play as we’d like you to believe. Even when it is necessary to switch platforms, you still have to go back and rebuild all the setups, integrations, and processes wineries created with their previous softwares.

Considering how important this issue is for our industry, I had hoped that some of our B2B publications would produce buying guides. Unfortunately, the limited number of wine industry vendors means these publications often refrain from taking a stance to avoid upsetting potential advertisers. I had hoped industry associations could fill this gap by employing experts to evaluate and recommend which tools and services are most beneficial for wineries. But most of them focus on supporting who becomes affiliate members versus which solutions are best for their members. Finally, tech companies themselves are often hesitant to take firm positions so that they can maintain neutrality within the tiny vendor community that services wineries.

So let’s deliver some balls and strikes —

Overhyped Technology —

Avoid Shiny Objects — I love generative AI, and it is genuinely one of the most important waves of transformative technologies since the iPhone, social media, e-commerce and search. Soon it will be woven into all your software tools as a invisible fuel to make every day tasks easier. However, the amount of AI-washing by companies trying to breathe new life into their products or inflate the value of what they are doing by saying they are using “Artificial Intelligence” is often just lipstick on a pig. ALL wine AI recommendation engines are junk science (especially the two claiming to be the industry leaders).

Software Pyramid Schemes — There are very, very few good use cases for blockchain and NFTs that are easy to implement and can scale. Most people pitching them have either drank their own Kool-Aid or micro-dosed their way into believing in a tech utopian use case that will never be. There are good use cases for loyalty programs or tracking provenance, but implementing them is not a simple exercise for both the brand and the consumer. So when Club dVin comes to tell you that NFT wine clubs are the future, you show them “Lucille.”

Software vendors —

Swimming with Lead Weight — We have a lot of vendors who are just garbage, and someone needs to say it. AMS may help your winery with accounting, but it is one of the world's WORST e-commerce and club tools. It acts less like sales enablement and more like a sale prevention system, and while it may make it easier for the finance team to reconcile the books, that’s not worth the way it limits customer acquisition and conversion.

The owner of e-Cellar once told me he was angry with me because I never promoted his solution. That’s because anyone with any integrity would never promote mediocre software to wineries when there are way better solutions in the industry for far less cost.

Predatory Software Pricing — You almost should NEVER be charged for software based on your production size or how much you earn in revenue. Software should charge you based on the volume of transactions they help you accomplish, the quantity of data they need to process, the number of users you have, or optimally, the features they give you. So when I encountered that both Enolytics and WinePulse charged based on your gross revenue. Even worse, I learned that some wineries pay more than $15K/year FOR BASIC ANALYTICS SOFTWARE, I was flabbergasted.

Fortunately, there is hope on the horizon. Stephen Mok from New Vintage Labs (who has a fantastic free newsletter, by the way) is about to release a souped-up winery analytics tool which will launch soon on Commerce7’s app store and then soon after on Shopify for between $49.95/month and $75/month!

I recommend you contact him ASAP if you are on C7 or Shopify and looking for a great analytics solution.

Texting is a Feature, not a Platform — Anyone using RedChirp plus an email system is doing it wrong. Not only are you paying a premium for SMS/MMS services that you can buy at a fraction of the price from SimplyText, but even more importantly, you can (and should) use Klaviyo because it is fully integrated. You can automate customer journeys versus the time and energy of cobbling solutions that don’t create a seamless customer experience.

If you are a Commerce7 Customer, the Digimatic app makes it easy to implement — https://digimatic.com/commerce7-to-klaviyo-integration/

E-commerce 101 — Shopify is a fantastic technology and e-commerce solution. It and Commerce7.com have become the industry leaders for price, functionality, and more. However, the Achilles heel for Shopify is that you need to combine a set of vendors with Shopify to make it work the same as C7 straight out of the box. C7’s recent acquisition of WineDirect’s stagnating e-commerce business has created ripples through the industry There is now the immediate opportunity to upgrade to better solution but equally a tidal wave of anxiety for producers. Change is always hard but made more so from the myriad of vendors crowing how easy it will be to move from WineDirect to their solution. Some of them are claiming it will be easy because they are “Shopify.” But they are not, they are just plug-ins and not all of them are created equal. Blowhards like WineHub, want wineries to think they can singlehandedly solve all of their DTC problem despite only being the club processing plugin and being far more expensive than other comparable tools like Awtomic — who are best in the breed for wine club processing and customer service and at a more than fair price — https://www.awtomic.com/pricing. Also what WineHub doesn’t mention that you are paying anywhere from 4% to 5%+ of your club revenue when you combine their costs plus Shopify’s processing fees not to mention compound subscription fees ranging from

Taxation without representation — Very few technology tools should charge a percentage of the transaction unless they are increasing revenue while continuously investing in R&D to make their tools better. In my humble opinion, the ones that help process and increase your revenue fall into that camp. Compliance tools that charge a percentage of sales should be immediately rejected. And candidly, ones that charge volumetric transactional fees that exceed those of email costs should also be rejected. How can Klaviyo can process hundreds of thousands of emails and texts at a fraction of the cost of what Sovos and DRINKS charge for compliance? It’s just data. The reason is because they know they have no competition and are predatory in their pricing. This is WRONG and needs to change. We need a better compliance solution

Service Providers —

The Good, the Bad and The Ugly of Service Providers — Any consultant who guides a winery in implementing Salesforce for its DTC tech stack should be immediately banished from our industry. Five major companies have collectively spent over $100M attempting to make it work, and all five have abandoned it.

If you meet an agency that says they specialize in . . . everything — RUN.

Finding good agencies in this business is hard because marketing and digital are no longer small jobs — those jobs require skills across a large and changing surface area. If you are looking for top-tier consultants for DTC, here are some companies I would hire —

• Egan Consulting — https://www.eganwine.com/ — specializing in branding and DTC
• Nonni Strategic Marketing — http://www.nonnimarketing.com/ — PR and International Brands
• First Pour — https://www.firstpour.co.uk/ — Without question, the best social media and influencer agency for wine.

I’ll have many more amazing vendors to add but I am running out of time to complete this article so I’ll add them in the comments as I remember. Favorite or bookmark this article to see additional comments with more companies that I would recommend in a heartbeat.

Reports —

Disinformation vs. Knowledge — Since Silicon Valley led the market by releasing vital information to help wineries succeed, this has become the de facto way to create thought leadership. Because we have such a dearth of information, nearly every report becomes relevant and is shared by the narrow group of B2B press outlets (barely five meaningful publications). And the amount of nonsense reports that are released floods the airwaves with poorly researched studies, reports that are only infomercials, or skewed information to match a narrative which echoes our post-truth reality. So when you hear someone quoting a WineGlass marketing report that only surveyed 1,600 US wine drinkers via social media, remind them that it is “a crime against data.”

If you are looking for good reports, always start here —

• Silicon Valley Bank Report — https://www.svb.com/trends-insights/reports/wine-report/
• Ciatti’s Monthly Report (now an online newsletter) — https://ciatticompany.substack.com/
• Terrain — https://www.terrainag.com/
• Rabobank — https://www.rabobank.com/knowledge/beverages

Press —

Abusing Power of the Pen— Too many wineries, vendors, and associations are scared to publically say what they all say in private. Yes, most critics no longer move the needle for sale but are a necessary evil to get past the retail gatekeepers. Yes, two of our most significant online wine publications are clickbait and have terrible ROAS (Return on Advertising Spend). Still, there are significantly few other options, and wineries I’ve inquired to would rather spend something with lackluster returns than get no returns at all. Yes, Jess Landers and the Chronicle’s editorial team have lost the narrative. They can’t decide if they are investigative journalists, the ones to champion the end of Napa, the inventors of the zero-zero trend, or Northern California’s natural wine guide. It’s a terrible waste of ink for one of the few publications that exposes our magical elixer to infrequent wine consumers.

We need better publications for wine and spirits but more importantly, we need publications that reach normal audiences to include wine and spirits content.

A Road Map—

Making wine is hard. Selling wine is harder. We live in turbulent times and there are a lot of voices championing a lot of choices. But what the industry really needs is actual experts taking a position how to build recipes for success. We need more honesty and transparency which platforms, technologies, and service providers wineries should choose and which they should avoid. We need more truth-tellers and more no-holds barred, objective evaluations of the industry players so wineries can avoid wasting money and time on companies that hurt them rather than help them. We need more Jeffrey Dean Morgans in the wine industry.

Know thyself — Take Inventory

Okay, now you’ve got the leadership agreeing to engage in the challenging digital transformation process, and the team is excited and inspired.

The first step in starting the journey of Digital Transformation is the boring exercise of taking inventory of a company’s internal and external digital footprint.

Externally, you should inventory all significant social media platforms, websites, owned URLs, online presentations or publications, third-party listing sites (especially Google or specialized industry platforms), marketplaces, etc., and who has primary access to those accounts. Logging them is as easy as using Google Sheets or Excel.

It’s also a fantastic time to do three things to build/rebuild foundations and are excellent practices for a small winery/company —

1. Ensure you have secured your business’s relevant social media handles and URLs so you never have to deal with a cyber-squatter. I’ll always remember when, at Vintank, we had to email some professional colleagues on Twitter because someone had scooped up the @OpusOneWinery Twitter handle and was promoting discounted wines from the account. Thankfully, they helped transfer the handle to the winery.
2. Consolidate login credentials around a single email (e.g., admin@company.com) and implement password management tools like LastPass, Dashlane, 1Password, Keeper, etc., to allow for sharing login information while maintaining security.
3. Build a file-sharing structure so all employees can access Google Drive, OneDrive, and Dropbox and be most efficient and effective with shared documents and assets.

Then, you need to do the tedious work of documenting internal software solutions and how those platforms work together. Document what tools operate your site: e-commerce, social media management, accounting, reservations systems, and more. It’s a simple list of platforms, departments, and account owners. Finally, I also recommend you take inventory of your brand pillars, KPIs, club amenities, customer personas, and customer journeys.

These are often challenging to obtain as they need to be created from scratch. Additionally, the team may lack experience which adds a learning curve and time.

Looking for instructions on how to map a journey? Here’s a great beginner’s guide and a nice software tool called Miro to make it easier. For data, you can use the reports from your e-commerce and wine club tools as a start.

Now you have all the ingredients to start the next steps for digital transformation — organizing the pieces, the next three key activities, foundational work, continual improvement processes, or high ROI activities.

Addendum — This is going to sound crazy, but you can tell a company will struggle incredibly with digital transformation if it cannot use shared files/document tools like Google Docs, or especially a tool like Slack. Four out of five companies that can’t grasp Slack have cultures that are too calcified to adapt. I recently joked with a colleague, “They can’t do jack if they aren’t even able to Slack.”

The early 2000s was a wild time for e-commerce, with every company thinking about going digital, and the wine industry was no different. Seeing an opportunity, I founded WineDirect in 2002 (originally and terribly named Inertia Beverage Group — IBG) to help wineries reach consumers increasingly interested in purchasing wine online. We would build their e-commerce platform on the backend and ensure everything ran smoothly on the front end. Demand was intense — we were selling our services to over 50 wineries a month.

But executing our vision was harder. Our customers had so many friction points that it was like walking uphill on the sands of the Sleeping Bear Dunes in Michigan: one step up, three steps back. Ultimately, we could only complete less than half of those new orders a month.

We had fallen into a common situation for startups: we had identified a product market fit — e-commerce software as a service for wineries — but were struggling to execute on product operations fit — execute on delivering our product as fast as we were acquiring customers.

In Startup Land, there is a threshold between having a viable product and being able to execute on delivery—one by which all companies are measured—the moment they achieve “Product Market Fit.”

It is that magical piece of the puzzle when a company’s solution matches the market’s needs. It means you have a product that solves a problem and is something people want and need. However, the number of startups who have crossed into that magical zone and failed is numerous. Most business books or VCs fail to mention two other essential layers that a company needs to achieve before they can actually achieve startup escape velocity — the point where they are in the flight path for true accelerated and rapid success.

After PMF, a company needs to find Product Sales Fit. It’s fine to know that you have a product that people really need, but you have not achieved PSF until you can consistently have an employee or a website sell it at a profitable price. You need to know the quantity of sales you can generate, sales per representative, conversion ratio, cost of sales (COS), churn rate, and average sale amount. Often, the problem is that the founder has led the company’s sales and becomes the iron pyrite of PSF. It gives the illusion of higher close ratios, longer retention, and lower COS. Modern VCs discount founder sales, making the close of a funding round harder to make with many of them. You need to build into your plan how you achieve this successful metric, or you will delay your ability to raise money or achieve success.

I can’t tell you how many companies we’ve found Product Market Fit, but getting others to sell it properly took so much time, training, and energy before we found a repeatable solution that we could use to scale. At WineDirect, the ability to teach wine people how to sell software, or software people to sell wine e-commerce, was years in the making, not to mention a pricing model that could sustain the R&D of supporting a SaaS company but is reasonable enough for a winery to buy.

Once you’ve found a way to a repeatable sales process and PSF, then one of the hardest fits of the business needs to occur: Product Operations Fit. So now you’ve found a product other companies need, you’ve found a way to sell it at a price that matches the ability to acquire customers and make a meaningful profit rapidly, but now the rubber hits the road. How fast can you implement and make customers successful using your platform? So many companies succeed in the final two of these phases but find implementing, supporting, and elevating the success of customers to be the most difficult challenge in running a software company.

As a small sampling, we had to overcome their inability to find their DNS information, help them transfer their customer information from legacy platforms (often problematic or dirty data), overcome their desire to go through a branding exercise, avoid design tinkering, wait for complete new photography or brand new content, ensure they had shipping rates and discounts properly loaded and tested, and so much more.

In those days, we were part of the early wave of e-commerce companies that charged a transaction fee (which is back in vogue), so we barely earned any revenue until a website was up and successfully operating. So, part of our Operational Product Success was teaching an entire industry how to sell wine online. That was everything from how to build their catalog, best practices for shipping costs, proper email marketing techniques, and even as simple as the basics of putting their URL on their wine label and business cards. The operational weight of both launching the wineries AND getting them successful never allowed us to achieve Operational Market Fit. To expedite that part of the process, our COO up-leveled our customer success team to help operate the basic elements of merchandising and email marketing. We took on the burden of operations to speed up the process.

I can’t emphasize how much you need to account for Product Sales & Operational Market Fit in your plan so that you, as a startup, can truly realize the success of your vision.

We need a new economic model to account for the debt associated with building something (and the debt accrued by not building) coupled with maintaining it. Perhaps you’ve heard of “technical debt.” Technical debt is a programmer’s term that represents the decision to choose a faster type of programming instead of a more stable, scalable code, realizing that you will most likely have to go back and re-code it in the future. But on a more fundamental level, it’s the understanding that things you build must be repaired, reinforced, or rebuilt over time. The more use/pressure, the faster you have to address repairing or reinforcing those items.

When you take this abstraction, ANYTHING you build creates technical debt. When you construct a house, a website, a relationship with a customer, a fence, or a garden, the clock starts ticking, and the debt begins to accrue. You can pay down the debt regularly or wait for it to accrue and pay it in a lump sum. Know that, like regular debt, technical debt carries interest. Deciding not to pay down debt incrementally or wholesale can have tragic results. For example, PG&E’s failure to upgrade or replace aging equipment or proper vegetation management resulted in the Camp Fire (and others) that burned over 18K structures and killed 85 people. For those old enough to remember, Y2K was a case study in technical debt and the extensive and incredible costs and effort it took to remedy it — despite it coming in like a lion and leaving like a lamb.

Why do I say this needs a new economic model? We often don’t associate buildings with technical debt. They’re treated as objects with completion, and rarely do we include future technical debt or the total costs of ownership (TCO). Instead, they need to be budgeted with a perpetual pay-down budget for eventual upgrades over time, the choices in original building infrastructure, and the advancements of technology/society that mandate upgrades. This is not just a suggestion but a necessity. We need a new economic model that accounts for technical debt to ensure the sustainability and safety of our infrastructure.

I’ve used the house analogy in the past, as it’s a great metaphor. Anyone who owns a house understands the costs over time. This is not just from family use but also requires the additional equation of time (decay and evolution). For example, think of a house built in the 50s. Over the decades, we’ve had continual improvements in technology for the original elements of the house (wiring, pipes, roofing, lighting) and new elements that were not even contemplated at the time (internet, solar).

Installing and retrofitting these are not easy or inexpensive endeavors. In fact, modern house loans should estimate the technical debt incurred during the loan term and include it as an addition to the mortgage with line items budgeting for repairs (TCO), upgrades/improvements due to time (technical debt), and a multiplier based on use.

This applies to everything we build. A website, for example, requires constant upkeep: new browser specifications, responsive design, new payment methods, improved shopping carts, ADA compliance, content, etc.., etc. It is a perpetual investment to keep it up-to-date and effective and to make choices intentionally for the appropriate size of the business. You can pay it down continually or allow it to run for years until you need to invest a considerable sum to upgrade it.

Building customer relationships also creates a TCO and accrues debt. This is too often overlooked unless you are truly a customer centric business. You need to invest to retain or react to the customer and to support new customer expectations, emerging technologies, and innovations. One of the easiest ways to understand if a company is serious about being customer-centric is to ask if they have a budget for customer retention.

What’s essential for modern businesses is the mental and financial shift to recognize TCO and technical debt in all activities. Unfortunately, business sustainability is not just about building things; it’s about maintaining and even regenerating operational initiatives. Regenerative business . . . I like the ring of that.

You may notice that I am writing in two places: here and on Substack. If you follow me on both, THANK YOU. I’ve chosen to split my time, energy, and thoughts between Medium and Substack because the content between the two platforms has distinctly different objectives. Transforming Wine will only have articles about the intersection of wine and tech. Deep dive profiles into companies and people. The challenges and opportunities where those two things collide. And commentary on new technologies and how they will impact wine.

Here, on Medium, it will be a smattering of Digital Transformation (hopefully always instructional), startup lessons, tactical guides to help wineries succeed in digital sales and marketing, helping tips for using tech tools, opinion pieces about the wine industry, some of the inside challenges and successes I experienced while building Pix, and also any random topic that I think is interesting and helpful to you, the reader.

If there’s anything you’re interested in reading about, please leave a comment, email, text, carrier pigeon or smoke signal me.

As you may have read, I am working with multiple wineries of various sizes to help them with a Digital Transformation process and documenting it to share with everyone. This first step, Step 0, is the prelude to the journey.

The first step for digital transformation starts with “priming the pump.” To ensure you have the best way to ensure people from so many backgrounds and disciplines speak the same language, you need to help align and inspire them with a shared understanding of thinking and operational frameworks.

For my part, I like to start a book club with every company I run. It’s a way to start building a common language. I found it works best if the leaders set reading goals as team objectives but, most importantly, participate in the conversation. And if you are the leader, YOU need to participate (even if you’ve already read the books). I once made the mistake of not joining; my leadership team didn’t take it seriously, and the book club became a nuisance and, candidly, a useless exercise.

I like to make Danny Meyer’s book the first primer to ensure that we inject customer-centric thinking and service into the culture of the organization.

• Setting the Table

Then I have a series of books that either speak to the challenges of startups, about user experience or inspire new ways of thinking about companies/products.

• The Cold Start Problem — Too many people underestimate the difficulty of getting past the initial product market fit, but how hard it is to build a customer flywheel. This book is an excellent primer to understand how other companies kickstarted their audiences/customers.
• The Hard Thing About Hard Things — A startup is a different animal. Most don’t understand the challenges and turmoil that always come with a new business, especially digital ones. This book is a guide for some of those tough business lessons.
• The Experience When Business Meets Design — Customer experience should always be at the center of your business — no matter what product or service you sell. Brian Solis understands this like very few people on the planet and provides principles and examples on how to make CX central to your company.
• Blue Ocean Strategy — When they zag, you zig. This is a great read to demonstrate to your team how you look for opportunities with high rewards and limited or no competition.
• Free — First, you can go on Amazon and get the audiobook for FREE. Second, the concept of free is something that widens a team’s aperture about conjunctive marketing.

A few Seth Godin Books — His style of provocatively using real company stories to articulate the changing nature of business always makes for a great read.

• Purple Cow — How do you stand out in a world of endless choices? This is a good way to help your team rethink what makes your company or product different. Similar to Blue Ocean Strategy.
• Marketing — certain corners of the wine industry have besmirched Marketing. I think it’s essential for all departments to understand the importance of this crucial business skill — engineering, finance, sales, public relations, and customer service. This is a great book that helps everyone understand marketing similarly.

Also, I am a giant fan of these two thinking frameworks with principles of creating, building, operating, and selling services or products. They are incredibly valuable for organizing teams around strategic goals, aligning on purpose and activities, helping reduce noise, and setting priorities.

• JTBD (Jobs to Be Done) — This framework helps eliminate wasted energy. It helps every department look for the ultimate purpose of any activity. Understanding purpose helps everyone align with the final customer’s actual use case (internal or external).
• Wardley Maps — This is an incredibly useful framework to understand what you need to buy, build, or rent and where you should focus, putting your resources and attention to best compete by understanding the key factors impacting your business. It requires a bit of practice or a professional to use it effectively.
• This video, in which swardley speaks, is a great and entertaining explanation of the framework.

Because I work in the wine business, here are a few content sources that we ask everyone to read so they get comprehensive understanding of the industry -

• The Annual SVB Report — This is the easily one of the most important reports in the industry.
• Rabobank Reports — The guys at Rabobank do a good job looking at all of alc-bev and have a penchant for examining some of the lessor-covered parts of the industry.
• Annual Sovos DTC Report — A decent benchmark of the DTC side of the business.
• Ciatti Grape Reports — There is no better reports to get a view into the current and future state of the industry by understanding the prices and demand of grapes.
• Joe Fattorini — His writing is absolutely brilliant and almost always on the mark.

I’ve partially returned to Twitter despite the toxic overload from Elon Musk’s ownership. However, so many of the same self-anointed pundits who have no operational experience or extreme product bias were pontificating and being the usual blowhards, recycling the same arguments-

• “Marketing is bad.”
• “We can best reach the new generation through natural wine.”
• “Wine has a quality problem.”
• “Commercial wine is bad — both in quality and for the industry.”
• “The way to get more consumers is education.”
• “What is “fine” wine (talk about angels on the head of a pin)?”
• “Napa and Sonoma wines are pricing themselves out of existence.”
• And so on.

Sadly, too many content creators regurgitate these topics, press releases, or company talking points without exploring the subject matter with journalistic integrity, perpetuating the confusion.

Like a large ominous cloud, the continual news about our industry is receding in volume, price, and consumers hung heavy over every conversation.

In the vendor space, I saw infomercial after infomercial about how *their* solution solved all the industry problems or selling yesterday’s ideas for tomorrow’s prices. Pancho Campo recently observed at his incredibly interesting Wine Future Conference, “How is it that ten years after our first event, we are still having the same conversation?”

I felt the same as I looked over the tech category and conversations about our industry. My statement, “Wine Tech is a graveyard of failure,” has been intentionally misconstrued, but it is absolutely true. No pure-play online wine company has achieved over $350M in revenue, nor is there a single digital wine company that dominates the consumer’s attention in the category like Uber, Amazon, OpenTable, Expedia, AirBnB, etc. Most large wine-tech companies make less than $10M, and the majority make less than $1.5M. Numerous small businesses have endured an incredibly long journey (“Over the past 25 years” — GMAFB) to become profitable, and they operate by providing their founders with modest incomes as lifestyle ventures. While they generate sufficient revenue to survive, they lack the financial capacity for significant growth or innovation.

I’m always exploring new technologies to see what can help make us better. After years in tech, I tend to avoid shiny new objects (my criticism of the over-hyping of Mastodon, the eventual lack of value in Clubhouse, etc.). I try only to recommend technology tools that will genuinely help a winery/retailer be more successful. I do think that generative AI is one of those technologies. I recently did a speech for George Christie and the Wine Industry Network (that will be my next post) with Justin Noland, who built The Wine Event only using generative AI. The new consumer-facing, generative AI tools are genuinely transformative to make people more efficient and effective, and learning to use them is imperative. However, they will become ubiquitous and virtually invisible as they integrate into the digital tools we use today. But as much as these new technologies interest me, we still have many industry fundamentals to master.

And that’s where I found inspiration. It was the problem I have seen throughout my career, even tangentially through my journey with Pix. We had close relationships with so many wine companies. We spent inordinate amounts of time guiding them and presenting advantageous opportunities (outside of Pix) but struggled to achieve consistent execution. And there lies the challenge — with very few exceptions, there has been no template for achieving digital transformation for wineries with different models (boutique, allocation, enterprise, imported) and retailers. And that fascinates me because, as the last industry to adopt digital tools universally, we need them more than ever to overcome the challenges ahead. As long as I’ve been here, I’ve witnessed so many people (myself included) touting the benefits of wine + digital: e-commerce, social media, search, mobile, and content are now essential tools for operating a business in a digital society. But with our industry, I think our success will be rooted in someone building roadmaps and actionable templates. For me, this is meaningful and fulfilling work. Multiple wineries have invited me to their Board of Directors to help them achieve success on that journey. Through those efforts, I can document our process, the challenges, and the successful paths for implementing digital transformation.

But, as I began this post, I NEED to write — and I need to be feral in my writing. Too many topics are muddied by people who have yet to do much to understand the category beyond their myopia or without any operational experience. There are essential topics that I need to write about and necessary for our industry: the digital shelf, content syndication, generative AI, DTC measurements, more intelligent segmentation, JTBD (Jobs To Be Done) for wine, the role of risk aversion in wine, the value of online wine platforms to wineries/retailers/consumers, marketplaces eat markets, the broken state of wine media (from the inside and the outside), glocalization, the limitations of wine marketing, big brands have significant responsibilities to attract younger and new consumers, methodologies for attracting new consumers, how *good* Flash Sale sites should be considered marketing channels — not only sales channels, the role of national e-tailers for building a brand. I hope to explore these topics and find more prescriptive ways for wineries to engage with these topics (by size) and, where possible, to illustrate examples. I also want to highlight companies and people that improve our industry in an interview series called Sips and Bytes.

Even though I’ve taken a sabbatical from Pix (I still think it is the best model for the wine industry), I’ll also keep writing about the platform on Substack — our story as I lived it, how it is genuinely beneficial to the wine industry, the challenges with wine and venture capital, the benefits of a healthy digital wine ecosystem, objective views on companies in that category, and the reason marketplaces eat markets. I’ll share why recommendation engines are junk science and where gaps exist in the market. Some topics I’ll repeat on both platforms.

I’m glad to be back, and I hope you’ll help me on this forever journey to help make our industry better and more successful using digital tools. Despite the challenges ahead, I truly think the future for our industry is also filled with so much opportunity.

My good friend Andre Ribeirinho asked me why, as a tech leader, I muted Clubhouse conversations on Twitter.

First, I’m not at all against Clubhouse. It’s exciting to have a new social media platform with a novel variety of engagements. In fact, you’ll sometimes find me quietly in a room, listening, learning, and analyzing its benefits for our industry. Industry analyst Jeremiah Owyang appropriately calls it a Goldilocks medium — one that’s just right for casual users, thanks to the ease and familiarity of voice. I think the platform is especially timely, considering our need for human connection during the loneliness caused by the pandemic. I also think the power of audio will be increasingly important, especially given the pervasive nature of voice apps.

As a platform, Clubhouse provides a means to create “live broadcasts”, where someone hosts a show based on voice. Like a conference call with guests, the broadcasts offer everything from insightful talks to casual conversations to infomercials, or even self-help chats. Like all social networks before them, they also offer platforms for toxic speech and misinformation. And, like them, Clubhouse is growing rapidly thanks to FOMO and our need to connect.

I get the hustle. A new platform makes room for new leaders who want to become its top influencer/professional. And that’s a good thing. Becoming a platform expert brings value to the medium. But with Clubhouse, the networking hustle is not just part of the formula, it’s central to it — the platform practically demands it. If you’re wondering what I mean, I’m talking about all the new influencers jumping on to offer you exclusive opportunities to build your business/email list/dewy skin.

The degree to which the hustle has become evident has already reached the level of programmatic satire.

Given the loneliness and boredom of COVID-19, the appeal of Clubhouse is obvious. Our need for connection and conversation is more significant than ever. Also, it matches nicely with wine. Our magic elixir enhances conversations, and speaking with our customers is a natural fit with our hospitality-focused industry. But as the world opens, Clubhouse’s forced synchronicity will become either its greatest strength — or a giant Achilles’ heel. The question for Clubhouse is: Will people want to schedule time for chats once the pandemic is over? Or will they want to return to their pre-pandemic on-demand, asynchronous social media and content usage?

As exciting as a new platform/technology is, I have mixed feelings. We are embarking on a new age of online wine, and we have so much work to do as an industry to improve the basics of e-commerce, email, SMS, data, video, social targeting, etc., that a new platform feels like a distraction from the fundamentals. I’m not knocking Clubhouse, and I’ve already seen great seminars and chats take place there. Still, I wonder if we, as wine-tech leaders, need to temper our excitement about yet another platform. What the wine industry needs urgently is better infrastructure to help it get to grips with the fundamentals of digital, rather than another shiny object.

In other words, I’m not against Clubhouse. It’s just that, right now, it feels like there are more important things to do.