Beyond Consulting

30: From Consulting to Chief Marketing Officer

In this episode of Beyond Consulting, sponsored by ECA Partners, we welcome with Jai Dolwani, a former Deloitte consultant and current Chief Marketing Officer of Winc. Jai joins us at ECA headquarters in Santa Monica, CA to share his journey from management consultant to leading marketing efforts for Winc, a fast-growing, modern winery with direct connection to the consumer, building a portfolio of brands for the next generation of wine drinkers.


The Beyond Consulting Podcast is hosted by Ken Kanara and co-hosted by Steven Haug. Steven Haug leads this week’s episode.



Steven Haug: Hey y’all, welcome to Beyond Consulting, the podcast dedicated to helping its listeners navigate a career after consulting. I’m Steven Haug, host of Beyond Consulting and Director at ECA Partners. Each week on the podcast, we host folks who have spent some time in consulting, but have since made a pivot or a career change. Before we get started I want to thank ECA Partners for sponsoring Beyond Consulting. ECA Partners is an executive search and on-demand consultant firm specializing in former consultants and private equity.

Today we have the pleasure of speaking with Jai Dolwani, Chief Marketing Officer at Winc, and former Deloitte consultant. Jai, welcome to Beyond Consulting and ECA headquarters.


Jay Dolwani: Thank you Steven, I’m very happy to be here.


Steven Haug: The first thing that I expect folks to notice when they look at your career is the speed. I’d love to start back toward the college days and learn a bit about how you got to where you are today.


Jay Dolwani: Yes, absolutely. I mean it’s been quite a journey. If I went back ten years ago to when I started college, I don’t think I would have imagined myself in this position. I didn’t really know what I wanted to do. I felt like it could be anything from consulting to accounting, since I was an accounting major, to entrepreneurship. I come from a family of entrepreneurs so I thought that was definitely a possible route for me to take, but I always told myself the one thing that I would never do is marketing. At the time I was just a young, ignorant kid and I probably didn’t respect the craft, but here I am. It’s been it’s been an interesting journey. I’ve taken a lot of different paths from consulting to start-up, to operations, to the marketing role that I have today, but I can say that I’ve always optimized for feeling passionate about my role and learning as much as possible. I’m somebody who gets incredibly bored if I don’t love waking up for work every single day so that’s what I’ve been optimizing for ever since I started my professional career five years ago. I’m incredibly happy and proud of how far we’ve come and I’m excited for what’s next as well.


Steven Haug: Great. Right out of USC you went to Deloitte?


Jay Dolwani: I spent a couple years interning for Deloitte, both after my sophomore and junior years, and then I chose to come back in the same exact role, full-time capacity, right after school.


Steven Haug: Good, so you spent a couple years with them and then it looks like you jumped into the start-up world, I would say.


Jay Dolwani: Yes, I ended up going to Bird. It’s actually a very interesting story. When I was in consulting, I did not know what I wanted to do next, but I was traveling a lot: Atlanta, New York, Ohio, you name it, I went there, mostly on the East Coast. I found myself, every morning and every evening, taking Bird scooters to and from work instead of hotels. It was just a product that I fell in love with and was incredibly passionate about. I’m like, “Hey, this is a company I would be really proud to work with,” so I decided to make the hop on over. I had no idea what I was doing in the start-up world, but I was passionate about the product and wanted to pursue that.


Steven Haug: Good, so Bird for a little while, and then where did you end up after Bird?


Jay Dolwani: Yes, so after Bird I went to a vehicle subscription start-up called Fair. They are a SoftBank-backed company. They actually recently sold, but they essentially offered consumers the ability to subscribe to a car straight from your phone, delivered straight to your door, as well as providing an offering for rideshare drivers to rent a car by the week and help them make a living.


Steven Haug: Perfect. Then after that, you ended up at Winc, where you are right now as the Chief Marketing Officer. Tell us a bit about what Winc does and then we can dive into your role specifically.


Jay Dolwani: Yeah that sounds good. Winc is building a portfolio of brands in the beverage space for the next generation of consumers. Winc originally started out as a wine club really dedicated against millennial and Gen Z consumers about 10 years ago. One of the things that our founders had noticed was that the entire wine businesses was so pedantic. It takes so much knowledge to actually know what you’re doing. For those of you who have ever been in a grocery store looking at hundreds of labels, not knowing what to pick, we all understand that. We really sought to demystify the world of wine and really make it accessible. We wanted to make it focused on occasion-based…enjoying a product with your friends for specific occasions. Over time, Winc started building its own products and brands, and realized that those products had lot of traction. Today we distribute our products, not only through our wine club, but also through traditional retailers in stores and restaurants all across the country. We really seek to sell in a diversified omnichannel way.


Steven Haug: Great, that is exciting. Right now you’re the Chief Marketing officer, but that’s not how you started at Winc, is that right?


Jay Dolwani: That’s correct. I joined as Director of Customer Experience. When I was at Fair, I focused a lot on customer retention and that’s very similar to what I was focusing on at Winc. I was really focusing on our website experience, CRM, customer support, essentially, everything we needed to do to improve the retention and LTV of our consumers. I was in that role for a couple of months, I then moved into the General Manager role for the direct-to-consumer business. Essentially, I was overseeing everything from acquisition to retention, conversion funnels, and the overall PNL of that business. I was also in that role for a couple of months and then moved into the Head of Growth capacity where I directly oversaw all of our marketing efforts, in addition to the PNL of the business.

Eventually, about six months ago, I moved into the Chief Marketing Officer role where I maintain all of the direct-to-consumer and marketing responsibilities. I’ve also taken on Omni channel brand building for our brands, so I’m also really focused on how we can scale through our wholesale channels, as well as other DTC functions like engineering, analytics, creative and brand.


Steven Haug: How many brands does Winc have at this point?


Jay Dolwani: A few dozen. Probably over 50 brands. I’d say there’s a core portfolio of about five to seven brands that we really focus on in an omnichannel way and the rest are really there to enhance the direct-to-consumer subscription offering.


Steven Haug: You ended up as a Chief Marketing Officer, but you mentioned that you didn’t think that that was where you’re going to end up. I want to rewind a little bit and go back to your consulting days. Your first day at Deloitte, what we’re thoughts then?


Jay Dolwani: How long is it going to take for me to make Partner? Yeah, this is my first thought. If you asked anybody that I had worked with at Deloitte, they would all tell you that I was going to spend my entire career there and I was going to become Partner because I had spent two internships there and I knew exactly what I was doing. I was passionate about it and really ingrained in the work. I always sought out to pursue that career path. One thing about me is that I get bored very easily, so a year and a half in I ended up getting bored, but when I came in there, I really came in with the intention of making it through the Partner track as quickly as possible. If you ask the people around me they would probably say the same thing.


Steven Haug: We’ve heard from a few of the folks on the podcast that the best thing to do as a consultant is to do the consulting work. What I mean by that is that there are two different types of mentalities that we see from some consultants. One is that they start as consultants and they’re working their way up the ranks. They’re doing the work. In the other group, they see consulting as a stepping stone to something else. Not that either one of those…one’s bad and one’s good, but it sounds like you were in it for the long haul at first, is that right?


Jay Dolwani: Yes, that’s what I thought. That’s absolutely what I thought.


Steven Haug: Do you think that that contributed to your success in consulting?


Jay Dolwani: Yes, I think so. What always terrified me about consulting is the amount of time that it would take to actually become Partner. I was just really focused on one step at a time. I really wanted to make it to the next level as early as possible and try as hard as I could to get there. At the same time, I was having fun and I was learning a lot. I really enjoyed showing up to work every day which, as I mentioned earlier, is something that was very important to me. If I have that passion and if I enjoy what I’m doing, then I’m typically going to be successful in the role over the course of time, so I think that definitely contributed to it a lot as well.


Steven Haug: How long did you stay at Deloitte after you decided to make the jump?


Jay Dolwani: Oh as long as it took me to find a job. I remember the day that I had been promoted to consultant, which is like the second level at Deloitte. I was looking at the career ladder and I’m like, “Am I really going to have to wait another two years for the next thing? I really don’t want to do that,” and I immediately started looking for jobs. I spent a lot of time in consulting in the healthcare space, so it was really looking at that space to start. I thought that was the industry that I would go into because it’s all that I knew. But, when I was riding a scooter one day, I was like, “Hey, maybe I should try this thing out,” so maybe just a couple of months? I pretty much knew it when I knew it and started looking and found my next role and moved on.


Steven Haug: How was the interview process?


Jay Dolwani: Obviously having the consulting background and the success within the firm to back it up really opened up a lot of options for me. I feel like I got a lot of interviews for roles that I wanted to be in and companies that I wanted to talk to, so I definitely found that the Deloitte experience coupled with the USC on the resume made that process so much easier. A lot of firms, especially the Big 3, if you have that on your resume you’re coming in with an inherent sense of respect from anybody that you’re talking to and that definitely helps as part of the process.


Steven Haug: I’m glad to hear that. It sounds like things have worked out extremely well for you post-consulting, as well on an accomplished career. What’s top of mind for you in your Chief Marketing Officer role? Folks in consulting who are looking at different career paths, what could they expect to be working on, day-in and day-out, if they did go to marketing route?


Jay Dolwani: I think one thing that I really love about my role and that is very different from consulting is that I can materially see the difference that I’m making on a day-to-day basis. I can see my work come to life and as the CMO I’m responsible for making the decisions that come to life. That’s something that I really enjoy about my role today that I wasn’t necessarily getting out of consulting. The beauty of marketing is you that put something out there in the world and can immediately see consumers react to that. To do that across ads, across digital product and website experiences, across building brands, putting on events, it’s an incredibly fulfilling experience. And marketing, coming from someone who is very skeptical, is a lot harder than people think it is. It’s really easy to do, but really hard to be great at because it requires such a delicate balance of art and science. Coming from a consulting background and an accounting major, I definitely lean towards the science side, so there’s always more to master. Although I’m a CMO, I would certainly not call myself an expert, or best-in-class. I think I’m always learning, every single day, which is exactly what gets me excited about it.


Steven Haug: Did you work on any marketing projects at Deloitte at all?


Jay Dolwani: Not even close. I was doing massive technology overhauls in the healthcare system. It was very focused on technology consulting. It’s something that Deloitte is very big in. It’s very specific to that firm, but there were these massive multi-year technology projects. It’s very, very different from what I’m doing right now.


Steven Haug: How did you get exposure to it, or did you just see it as an interesting problem and something to jump into?


Jay Dolwani: Yes, it was a little bit of exposure when I originally joined Winc. In the Customer Experience role I was adjacent to the marketing function. I think, over time, as I started to learn the business a little bit more, especially in the General Manager capacity, I started to see areas of opportunity where I could really bring the problem-solving mentality that consulting teaches you and data-driven approach to improve the way that we did marketing. From there I started diving really deeply into that world. I got a lot of knowledge from podcasts, a lot of knowledge from Twitter and I just tried to apply everything that I was learning and soaking up from the world, combining that with my strategic and data-driven background to become an effective marketer.


Steven Haug: You mentioned the consulting toolkit translating very well, probably into all the roles that you’ve held would be my guess. What part of the toolkit wasn’t there when you made the jump?


Jay Dolwani: I think the one thing that consulting really helped with was soft skills. The soft skills and approach–really dealing with incredibly difficult clients and partners, being in there in those boardrooms, in those meetings, addressing questions that you have no clue what the answer is to or developing a presentation anticipating all of the questions that somebody is going to ask and being able to stand up there and confidently speak to that in the moment I think is something that consulting really helped with. What was missing was how things actually happened in startups. In consulting, there’s a lot of Excel work, a lot of pre-analysis, a lot of making perfect PowerPoint decks that are literally perfect to the pixel, and as soon as I joined Bird I realized that a lot of that didn’t matter. They just wanted to execute and they wanted to see results. So switching from this intense planning process, making a bunch of decks and doing a bunch of analyses to actually doing the work and executing, was a mindset shift that I got when I came into Bird. I remember one of the first weeks I went into a meeting, my first really large, cross-functional meeting and I thought that if there was a meeting, there has to be a deck, so I stood up there with this 80 page deck. About 30 seconds, in somebody stopped me  and they were like, “Are you new here?,” because to them, it was this absolute ridiculous notion that I spent time putting together an 80 page deck. That’s when it hit me that this is not how the real world operates. That was a little bit of a mindset shift in terms of how start-ups operate, how work gets done and what people spend their time on in companies like Bird and Winc.


Steven Haug: It sounds like the pace is pretty similar. Would you say that it’s a high-speed environment both in consulting and in the start-up world, but it’s just that the measure for success or what you’re expected to be spending your time on is quite different?


Jay Dolwani: Yes, I’d say pace from the expectation of deliverables, now what those deliverables are has really changed, and one thing, as I was saying really opened up my eyes was that it felt like in the startup world, or in the tech space, a lot more work actually gets done. Whereas the deliverables in consulting is a lot of making up from lack of knowledge in the industry because, in reality, you’re a year or two out, for the most part you’re switching clients in different industries, in different spaces and you’re spending a lot of time making up for what you don’t know: research, decks, expert calls, all of these things. Over time, it was really interesting at the start where I felt like I was learning a lot but then after that, I was like, “What am I actually accomplishing here?,” and “What’s the impact that I’m actually having?,” and switching to actually doing the work and driving results is what changed. At Bird and Winc, I’m measured by KPIs and results of the business, not how pretty my decks are. That was incredibly refreshing for me when I made the switch.


Steven Haug: Interesting. I can tell you, whenever we’re interviewing consultants for various roles with our clients, eight out of ten times, the motivation for leaving a consulting firm is because they want more ownership. That is what we hear often. It sounds like that rang true with what you found, at least, even if that wasn’t your motivation for making the jump.


Jay Dolwani: Yeah, I think that’s pretty true. I’d also say that that’s what a lot of people think that they want. Then, when they’re placed into that expectation and reality, it’s so different. Three months into Bird it was such a culture shock, I almost quit and went back to consulting. I was like, “I don’t know if I can do this. This is so different.” I’ve hired people directly out of consulting as well and I’ve seen it work both ways. For a lot of people, it’s a huge culture shock and it’s what they think that they want. They want more ownership, they want to deliver results, but then when they’re held accountable to that, it becomes a little bit of a shock, of like, “Wait, I’m actually supposed to do this? I don’t know if this is for me.” It’s what a lot of people think they want. I certainly thought that. I almost was unsuccessful, but luckily enough, stayed along with Bird and eventually found my way.


Steven Haug: Good. Speaking of things that we don’t know, let’s say I came to the table and my picture of marketing was from Mad Men. What am I missing? How is it different today versus that image I think a lot of us, just given pop culture, think of as marketing?


Jay Dolwani: I think it’s almost a difference of advertising versus marketing. I can’t really speak to the world of advertising, but most of what marketing is today, especially as you see some of these newer, direct-to-consumer businesses is, like I said, a mix of the art and the science. It’s incredibly data-driven. We’re talking about advanced analytics, regression models, attribution methodologies coupled with consumer psychology and that’s what you see a little bit more in Mad Men. What’s the consumer actually going to relate to? What’s the hook that’s going to keep them watching this piece of creative? What’s going to make them click? What’s going to make them go down the funnel and eventually convert? I’d say 75% of it is on the data side and once you have the data you have to understand the limitations of it. That’s really where the creativity comes in, in terms of how you actually action on that and what it’s telling you, versus what it’s not. I think a lot of it is, it’s an incredibly data-driven field to be in today and, of course, data-driven marketing is like this buzzword that’s been thrown out there for so long, but what that means in reality is not looking at top level KPIs, it’s really, really understanding across various consumer touchpoints. Everything from a billboard to an ad on Facebook, to something they heard their friends say to them Googling something and seeing a top ten list. What is the impact of each of those marketing touch points and how do you justify an attribute spend to specific channels and what is that overall funnel-in journey look like? There are some incredibly complex problems to solve and that’s, I think, the difference obviously in Mad Men. It’s a little bit more simplified. It’s focused on advertising and consumer psychology, but this whole world behind it, that’s been incredibly fascinating for me.


Steven Haug: Interesting. The distinction between advertising and marketing, I’d love to hear a little bit more about that. At Winc, do you have an advertising department


Jay Dolwani: No.


Steven Haug: What would an advertising project look like versus a marketing project?


Jay Dolwani: I think it really depends on the types of brands that you look at. If you’re looking at smaller, e-commerce brands, which is what we’re very focused on, we’re talking about performance marketing for the most part. Advertising is closer to what people define as brand marketing. Now, I believe you can do both at once and have brand infused into your performance marketing, but if you look at Super Bowl commercials, what apple puts out there, what Nike puts out there, I’d say that’s really the world of advertising. If you look at what you see as you’re scrolling through TikTok, Facebook or Instagram, that’s really the world of marketing that I live in.


Steven Haug: Right. I think that’s a really helpful distinction for our listeners as well. You mentioned that you didn’t touch any marketing in your consulting days. I think that’s often true. What do you think consultant should be, if they want to get a taste of marketing, or dive a little bit deeper into it to see if it is something that could get them excited, what could they be doing, what could they be looking into to help them think through that decision?


Jay Dolwani: So, they’re probably not going to be successful at this, but to tell them whether or not it’s something that they could be passionate about, I would encourage them to find a product on Alibaba. I would encourage them to build a website and see if they could sell that product. If they can do that, or if they find passion out of doing that and figuring that out, I’d say marketing is a great space to do it in. This is something that could be done in the span of 24 hours of like, “Let me try and do this thing and see how I can execute.” I think the easiest way to figure out if you’re passionate about something is not to spend endless time reading books or articles or taking online courses, just do it. It’s so easy to execute and see how you like it.


Steven Haug: If you could start your career over again, would you still jump into consulting first?


Jay Dolwani: No, I probably would not have gone to college.


Steven Haug: Really?


Jay Dolwani: I think that there’s so much wasted time and opportunity cost, and obviously, I’m very lucky in terms of how things turned out, but it’s very possible that it would not have turned out this way. I’m very lucky that I’m passionate about what I do now but I could see myself also still being a Deloitte right now. For a lot of people, that is the right move and that’s what they’re passionate about, that’s what they enjoy doing. That’s not for me. I think going to college and getting a job in consulting has made me very comfortable with getting a paycheck and continuing to climb the corporate ladder. Whereas I felt like if I didn’t do that, I would be a lot more entrepreneurial from the start, and perhaps find myself in a similar role and position, but obviously with the higher likelihood of getting there. I think the opportunity cost of life is just so great in those early years from 18 to 25 that I would have spent a little bit differently. I would have spent it building things, building businesses, knowing what I know now. But back then, I’d have probably thought that growing up in an immigrant household that that would probably be frowned upon and I was probably a little risk averse myself. I think I would have taken my approach to life very differently. The first time where I really took a big risk of not climbing the corporate ladder and just doing something because it’s what I wanted to do and what I was passionate about was when I made hop from Deloitte to Bird. I took a 50% pay cut, but it was one of the most rewarding years of my life and I wish I did more of that, younger.


Steven Haug: Good. I think that’s helpful advice because we often hear this when we’re talking to folks in consulting, that the career path is laid out fairly nicely. You’ve seen people go through it already. There are dates on your calendar when you can expect promotions and raises and those sorts of things. Even outside the start-up world, other companies lack a lot of that structure, some in positive ways, some and not so positive ways. I think the idea of getting comfortable with that risk, for the sake of, not only the possible upside, but also the opportunities to learn is a great piece of advice. What I’m taking from your thoughts about not going to college is that jumping from one role to another in this era where entrepreneurship is valued very highly and whenever failure, often, can be a positive on a resume. The idea is that moving from one role to another is such a large learning curve in a lot of industries that you’re going to fail at it anyway, and you’re going to have to just learn it all in the first six months there, so why not just start by spending a few years.


Jay Dolwani: Yes, there’s no more valuable learning than trying to do something and failing at it. It’s very possible that I would have chosen not to go to college, try to start a couple businesses, been a colossal failure, and ended up going to college anyway, but I think that’s okay. At least you’re not wondering “what if” and at least you would have learned a lot. I think in a world where everything is available online, an expert in a space your passionate about is just one cold message away, I don’t think there’s any reason not to start to take some risks and figure out what you’re passionate about and start to execute against it.


Steven Haug: How long was Winc around before you joined?


Jay Dolwani: Winc’s been around for about ten years. I’d say it really came on the map during the pandemic when everyone realized that you could actually get alcohol delivered to your door and the wine subscription model totally took off. I joined a few months after that.


Steven Haug: Can you tell us the story behind the company itself, because I noticed that wine consumption in the US has doubled in the past ten years, 20 years, something like that? It was stagnant from the 1980s up until almost 2000. Did Winc come about trying capitalize on that or is it more than a wine company?


Jay Dolwani: I would say today we probably see ourselves than more than just a wine company, but I think at the inception it was really a couple of things. I think, number one, wine was incredibly inaccessible. In order to get the story and try wines from around the world, you really relied on tasting rooms. It was really bringing that tasting room online, where you could get the story, you could understand where it was from, what it’s paired well with and you could get that delivered right to your door. You could get it from one spot: a wine from Argentina, a wine from South Africa, a wine from Napa, and a wine from France, all at once. 11 years ago, that was a pretty revolutionary concept if you think about how far e-commerce has come in that time. It was relatively nascent back then, especially as it pertains to this wine club or wine subscription model. Really paving some path in terms of accessibility of wine to the next generation of consumers is how it originally started and I think focusing on that audience has been in our DNA ever since then. Now, even though we’ve focused outside of wine, we’re really focused on bringing people together and creating great experiences by creating these innovative beverage alcohol brands for those next generation of consumers, whether it’s in wine, whether you drink cocktails, sake, etc., that’s really what we’re focused on.


Steven Haug: Running a marketing department, are you thinking mostly about social media apps, are you still sending out mailers? What are some of the levers or avenues that you think are really important for someone marketing in a fast-growing company?


Jay Dolwani: I think it’s really dependent on what you want to execute, so I’ll give two examples. One is we do marketing for, which is our wine club. The beauty of running marketing for an e-commerce businesses is that everything is testable. Of course, we have our key social media channels, we work with influencers, we work with affiliate partners, we advertise on Google, but if we wanted to do something like send direct mail, great. Run an experiment. If we wanted to do TV, we’ll run an experiment. We’ll understand how it contributes to our overall media mix and make data-driven decisions and then continue to re-test this hypothesis and those tests that we’ve done one or two years ago to make sure, you know, consumers psychology and mindset shifts all the time, so to make sure that what we’re doing is still relevant.

Another example of marketing where it really requires a lot more knowledge of consumer psychology and, quite frankly, a lot from marketing expertise, is a type of marketing that we’re doing for our brand. So Summer Water is our top rosé. It’s one of the largest rosés in the country, and this year was really the first year that we put a lot of marketing power behind it. Now for summer water, most of the sales are on the wholesale side of the business, so it’s a three-tier distribution channel where we go through distributors and they sell it to retailers, and retailers want to see that product going off of their shelves. You can’t really run a digital ad and then expect that person to drive on over to a Target and pull that product off the shelf. You have to think a little bit outside of the box. That’s really focused on key geographies in real life events, key partnerships with publications, strong PR, as well as the digital aura behind that, so it’s really different types of marketing depending on the goal that you’re trying to accomplish and the channel that you’re trying to sell into.


Steven Haug: Do you work with the wine makers pretty closely?


Jay Dolwani: Yes, so we actually have an internal team of wine makers. We don’t actually own any vineyards or production facilities. What we do for the most part is we enter into grape contracts with existing vineyards and our wine makers are going on the ground, picking the grapes, helping create that wine and are obviously responsible for the end product itself. That allows us to be incredibly dynamic in how we source.


Steven Haug: That’s great, are you working backwards at  all? In your role, you’re seeing tons of data and you’re probably in Winc, one of the people closest to the consumer. Does any of that data trickle back down into the wine itself? Maybe making adjustments with labels…?


Jay Dolwani: Absolutely. That is the key way in which we produce products and brands and think about innovation. We have the beauty of this online platform where we can understand what products are selling. We can also get into a few key experimental areas, put it on the site in a very low risk way and see how it pulls through. We could look at click-through rates relative to other products, we could look at purchase rate, repeat orders, reviews, etc., to really inform our production plan for the following year. Of course there’s going be a little bit of delay when it comes to wine since we’re on an annual harvest cycle, but we definitely use all of the data that we get from our consumers, what they’re telling us, what’s pulling through, to help us innovate into future brands and products.

If you had two products with the same exact juice but different labels, and one of them is pulling through more than the other, and one of them has higher reviews than the other, maybe that one has a stronger label and brand story that consumers are just connected to. One anecdote that we like to use is that if a wine maker tells you a good story about a glass of wine you’re guaranteed to like it. A lot of it’s about that storytelling in terms of what’s behind it, what’s behind that bottle.


Steven Haug: That’s funny, is that a real example? Do you have same wines but with different labels that have different ratings?


Jay Dolwani: No, no, but it’s an example of something that we could do, and we have that consumer data and that consumer connection to tell us that.


Steven Haug: Good. What are, as much as you can tell us, are there any major projects on the horizon that you’re very excited about at Winc?


Jay Dolwani: Yes, I’m actually really excited about a lot of our upcoming products in the innovation pipeline. I know we were talking about Winc as a wine company or a beverage company, but really expanding outside of the wine space is really interesting, as well as continuing to create products in the areas of wine that are that are growing…so, organic, better-for-you, types of products, prosecco and bubbly is a large-growing category, orange wine is a large-growing category and of course, the entire ready-to-drink cocktail trend is large and growing, both wine-based and spirit-based. I’m really excited to see consumer adoption reaction as we expand out of wine, especially as it pertains to the membership, because so many people have joined it to be part of a wine club. When we’re able to offer them all of that plus other beverages that they consume, I think that will create a really exciting experience and a go-to shop for anything the next generation wants to drink.


Steven Haug: That is exciting. Whenever you say, “Expand outside of wine,” you’re thinking about those ready-to-drink cocktails and other beverages primarily?


Jay Dolwani: Yes, we launched a sake a few months ago on the website, so we do have some experience outside of wine, but I think everything from, think of categories that we could possibly get into…we’ve also done hard ciders in the past, we could do hard kombucha, we could do ready-to-drink cocktails, seltzers…there are a lot of possibilities out there. Obviously, we know that today’s consumer drinks more than just one type of beverage and so that’s really exciting to be able to fulfill all of their needs across that.


Steven Haug: Are you shipping globally or just in the LA region, in the United States?


Jay Dolwani: We ship in the United states, direct-to-consumer, but our products, especially Summer Water, which is our largest brand, is available in retailers nationally. Canada, Mexico, I believe we’ve in Costco in Mexico, all over Europe, India, Philippines, etc., I definitely seen our products available across the country or across the globe, which is really exciting.


Steven Haug: It’s quite an operation. How many people do y’all have at Winc at this point?


Jay Dolwani: We’re at about 80 people full-time.


Steven Haug: Wow, okay, I expected that number to be higher just given the reach. I’ve seen Winc branding, and I may have gotten some promotional materials and different types of purchases, food delivery, that sort of thing.


Jay Dolwani: Sure, yeah.

Steven Haug: That is very impressive impact for a lean team.


Jay Dolwani: Yes, and that’s one of the things that I love about the startup world, although we are publicly traded company, we’re a small company and we’re lean and people wear multiple hats, but it enables us to do everything that we do with the team that we have today.


Steven Haug: Were you there for the IPO?


Jay Dolwani: Yes, that was last November.


Steven Haug:  Wow. Well, congratulations!


Jay Dolwani: Thank you, thank you.


Steven Haug:  Has your work changed at all?


Jay Dolwani: It’s definitely…we probably picked the worst time to IPO. What’s happened to  growth stocks, especially in the consumer and direct-to-consumer marketplaces, has not been particularly great over the last six-to-eight months, but I think the key thing for us is to make sure that being public doesn’t change anything in terms of the actual work, to keep our heads down, continue to execute against the strategy and the results will speak for themselves.


Steven Haug: What are some of the major accomplishments that you’re most proud about Winc?


Jay Dolwani: Yes, a couple of things. I think one is when we think about the direct-to- consumer business, one of the things around wine clubs is that all of them have this introductory quiz that they promise you that some fancy algorithm will somehow magically match you to the perfect wines that fit your specific taste buds. All of that is a load of crap. One of the things that we did at Winc was really seek to deliver on a quiz that was relatable and made a lot of sense. Instead of asking whether a consumer likes their coffee with milk or not, or whether they prefer their orange juice with pulp or not, we just ask them about flavors that they like and we choose wines with those tasting notes, foods that they like to eat, and pair wines with them that match with their lifestyle and that would pair well with those foods, countries that they’re interesting in trying products from, and then we tell them why we selected that box for them. We really tried to demystify that entire process, which is really unique in the wine club space if you look at the competitors, so I’m really proud of that.

Then the second piece is the way in which we think about omnichannel marketing. I think we are unique in that we are a portfolio of beverage brands that sell online and in-store and thinking about how we can craft a marketing strategy where a single marketing dollar not only derives positive ROI digitally on the direct-to-consumer business, but also increases brand awareness so that that product is now pulling off of a shelf faster has been really interesting to go after. We’re seeing some great results with how we’re doing that for Summer Water and other brands this year.


Steven Haug: Good. You’ve taken some major risks at a few different points in your career. Just as its helpful for our audience here, I think that those stories can help prepare them for the times that they take those risks. Were there any that you were particularly worried about?


Jay Dolwani: Yes, I think going back to the anecdote I shared about Bird, you know I took a risk to pursue my passion. I took a 50% pay cut, I had to sell my house because I could no longer afford the mortgage, and move in with three roommates. That was a huge risk that I took and a huge life change for myself. Then, three months in, I was so miserable. I wasn’t fitting in with the culture and I was on the verge of quitting. I was actually looking into going back to Deloitte. Luckily, we had a major restructure and I had my role change. I was focused on this new ventures concept, I got a much better manager that I could more closely relate to, but I was this close from that risk not being successful. I’m glad I stuck it out just a little bit longer because I would have missed out this whole, large world of opportunity. I would say that my decision was very close to being a poor one. I probably got lucky but that’s okay. If you take a risk and it doesn’t work out, really in the grand scheme of things, like we’re all in the top 10% of the world by being born in the United States and having the opportunity to work in consulting. These aren’t really risk compared to the broader scheme of things, so I just keep that in mind and continue to go after what I feel like is important. Just thinking about the opportunity cost is that of like, we all have one life here, we don’t know how long that is, so we might as well make the most of it.


Steven Haug: How did bird win you over? As a recruiter, I can tell you that telling someone, “Hey, you gotta take a 50% pay cut to join this company,” that’s a tough story to tell to convince someone to join your organization.


Jay Dolwani: Yes, well, at the time they were the fastest growing company valuation-wise. They were the first company or the quickest company to achieve Unicorn status and they were at the height of their growth. The promises were around how the equity that they were offering would be worth hundreds of thousands or millions of dollars in the future. That equity is now worthless, but that was the promise in the allure that brought so many of us into Bird. We actually had the option to take higher cash or lower cash, higher equity or lower equity packages. I chose the lowest cash package with the highest equity because I was such a sucker for that story.


Steven Haug: That’s exciting. I think a lot of us can relate. You join a start up for a lot of reasons, and one is because you want to be a part of the growth story and if you’re really buying into that, then I think you make that that decision every time. Well good Jai. Is there anything else that you think would be helpful for our listeners to hear about your story?


Jay Dolwani: Yes, the only thing that I would caveat with is that this is my story and my career that I’ve optimized for what I care about. I think nothing is definite and everybody has different passions for some people staying in the world of consulting, or getting their MBA makes the most sense for them. Also for others, they may not be in a position to take as many risks as I did. Perhaps they have a family back home that they have to take care of, etc., so I say this with the caveat of everybody comes from different backgrounds and everybody is optimizing for something different. I’ve been optimizing for what’s best for me and my personal situation, but I really encourage everybody to not take any of this as definitive or exactly what they should do, more so as context in another experience that they can help use to inform their decisions hopefully.


Steven Haug: Well good Jai, thanks so much for visiting ECA headquarters and for joining us on Beyond Consultant.


Jay Dolwani: Yes, thanks for having me. It’s been a great time.



Connect with Jai on LinkedIn and visit for more information.




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