Sigma Prime Ventures' Jere Doyle: a Life Lesson in Perseverance banner image

Sigma Prime Ventures' Jere Doyle: a Life Lesson in Perseverance

Jere Doyle is a Managing Director at Sigma Prime Ventures. He joined the firm in the fall of 2015, after spending time as an active member of the Boston startup scene, where he operated as either a mentor or seed / angel investor.  

Prior to becoming an investor, Jere founded Prospectiv, an online performance marketing services provider and operator of EverSave, a leading daily deals website. The company was acquired by Affinion Group in 2011.  

Keith Cline: Tell me about your background.

JD: My mom and dad were from Boston, but I was born in Europe and spent 12 years there, between Italy and England. We would come back to Massachusetts and go to the Cape every summer, so I think of myself as being from Cape Cod.

I didn’t come from a family of entrepreneurs. My dad was in the Navy at first and then he climbed the corporate ladder at a chemical company called Rohm and Haas. I have two brothers and a sister, who all decided to take more of the corporate journey.

I was different. As a kid, I was always dreaming of different business ideas. For example, down at the Cape one summer, I learned that a clock factory at the end of my road needed old newspapers to cushion shipments. They would pay a penny a pound. I went to a bunch of neighbors, collected their old newspapers, and sold them to the factory. I realized that the business would scale much faster if I had some help. I hired my brother and two of my friends. We scoured the whole town and we would collect between $5 and $20 worth of newspapers each time. I split the money between four of us. It taught me that you can take something that was earning a few nickels and dimes to building a team where it would expand and make considerably more money.

My dad went to Boston College. My brother and sister graduated from BC, too. During high school, my family was living outside of Philadelphia, so I applied to Penn State and thought I’d go there for college. But I ended up selecting BC. I guess it was the natural selection, as I always considered Boston as my true home. I had four great years there.

This led me to my next journey in business. The summer between my sophomore and junior year at BC, I went to Spain’s Canary Islands for a unique opportunity. Instead of my previous summer job of doing dishes on the Cape, I traveled abroad for a marketing job, where I helped to sell condos over there.

I had a very small apartment. I was all alone. I didn’t speak Spanish very well and I just remember it was really hot. I was homesick and wanted to quit and come back to the Cape shortly after arriving, but I felt like I had to at least stick it out for a week to give it a fair shot... then two weeks, then a month. As time went by, I got more used to it and ended up staying the whole summer there. It was life changing and taught me an important life lesson of perseverance and to never give up.

I was working for a marketing company that was working with real estate owners and developers who were looking to attract potential buyers for their condos. Our company was focused on customer acquisition, as we would book consumers for a vacation stay at a property. Then there would be the opportunity to pitch these potential buyers to either purchase a timeshare or they could buy a condo outright.

KC: What did you do right after graduation from BC?

JD: Not only did I end up working abroad for the same company the following summer, but I ended up working there full-time after I graduated from Boston College. I helped the company expand with offices in new locations like Sweden and Holland. 

After four years of traveling a ton and getting married, I decided to come back to the U.S. and attend Harvard Business School.  

After graduating, I originally accepted a job at General Mills. At this point, my wife and I had started building a family. I thought this would be my time to take a job in a large company and start climbing the corporate ladder. That’s when I got a call from my old boss. They wanted me to come back and run the company in Europe.

They had over-extended themselves by expanding outside of marketing and became an actual developer. The company was in really bad shape. I was fortunate to assemble a great team. We ended up turning things around and getting the company back to their core operations as a marketing organization. We sold it in 1998 and I stayed on for a year to fulfill my obligations.

Jere Doyle Traveling
Doyle traveling in Masada, Israel

KC:  Tell me the story about Prospectiv, the company you started.

JD: Afterward we sold the company abroad, I moved my family back to the U.S. It was 1999 and the internet 1.0 bubble was in full bloom. I started a new company called Prospectiv. We had a vision to help local retailers use the internet to drive people into their stores through coupons via email. The idea was fundamentally sound, but it didn’t work for SMBs. The internet was still too new and they didn’t know how to use it as a marketing tool yet. We ended up shifting to larger brands like TJMaxx, Staples, and Office Depot.

We raised about $11M through four rounds of funding. We were fortunate, as we raised our last round right before the markets plummeted in 2001. We stayed the course by working with a lot of retail and CPG companies and then moved over to to healthcare and pharmaceutical companies. We had a good run for four to five years. We were profitable, with 150 employees in Wakefield, and we paid all of our investors from our cash flow.

Then the recession of 2008 and 2009 hit. Companies started cutting their advertising budgets. We went from a very profitable company to one that was losing money so quickly. We had to make some hard decisions and lay off a bunch of people.

KC: Can you talk about the expansion with and an acquisition by Affinion Group for $30M?

JD: It was a dark time, but we noticed the rapid growth that companies like Groupon and LivingSocial were experiencing. They were doing coupons for local merchants, basically what we started out to do back in 1999. After talking to some merchants who were using these services, we got some great feedback. They loved the customer flow that deal sites like Groupon generated, but they hated the one and done! They didn’t know anything about the customer or how to get back in touch with them.

We already had the core customer acquisition DNA in place, which included a solid customer retention program for our big branded customers. So we decided to offer a new service to SMBs and called it Eversave. We offered daily deals in the form of coupons for merchants. But the key to our service was the backend. Our clients could keep in touch with their customers by offering a program of offers, not just one and done, through our triggered drip email system.

I went on to build Eversave while another executive ran Prospectiv’s core business. We grew quickly, launching in 25 cities with an inside sales team in Wakefield. Groupon and LivingSocial had raised massive amounts of money and were outspending us, but we were keeping pace with a fraction of the money. We were at a crossroads with the business and had to decide whether to raise capital or sell the business.

It was a hard decision, but it was good timing for a liquidity event for the management team and employees who had been with us for a long time. We sold to the Affinion Group in Connecticut, who had 7K employees and billions in sales.

KC: Do you have any interesting or fun stories to share from the web 1.0 bubble years?

JD: It was a crazy time, with lots of whacky stories. I remember we were on the west coast raising money and had been out there for over a week, literally criss-crossing all over the place. We were in San Diego and headed to LA for a meeting. On the way, we ran out of gas about 30 minutes from the meeting. I was with our CFO. We jumped out of the car and luckily found a gas station that loaned us a gas can. We got to the meeting on time, smelling like gas fumes, and somehow they still invested in the company. It was another lesson in perseverance.

KC: When did you start making angel investments?

JD: After I left the Affinion Group, I got introduced to Ty Danco. I’m not sure if he remembers, but we met at the Marriott in Cambridge in 2012. He took me around and showed me Dogpatch Labs and Techstars. Prospectiv was based in Wakefield, so I had no idea what was going on in the Boston tech scene and I was blown away. I didn’t even know what an angel investor was!

I started helping out a couple of entrepreneurs like Jebbit (founders from Boston College) and Rocketmiles. Since I have a lot of experience in customer acquisition, my skillset was of interest to companies who all needed help in that area.

A year later, I had invested in five to six companies and I was an angel investor. It was my passion for working with entrepreneurs that led me down this path and I realized this would be my next chapter.

I realized that it would be hard to keep up with the pace of writing $10K to $50K checks in startups five tp six times a year for the next 10 years, so I approached some mentors who were from the Cape about putting a fund together called the Oyster Angel Fund. Now that I had a few million dollars to invest, it became a full-time commitment. Over the next year and a half, I made 25 investments. I was enjoying every minute of it. I was helping entrepreneurs build out their teams, assist with the product roadmap, raising money, etc.

KC:  What were you guidelines for making angel investments?

JD:  I had three rules:

  1. The company had to be in Boston, as I didn’t want to be flying around. I would only make an exception if I knew the founder well.

  2. I had to love the founder / CEO and be able to help them and add value to the company beyond writing a check.

  3. I had to both love and understand the space the company was trying to disrupt.

KC: Why did you join Sigma Prime?

JD: Sigma’s been around over 20 years. They have a great reputation for backing some great companies, and they’ve built a great firm. First, I really liked their focus. We primarily do Series A rounds, and I see a real opportunity here to build one of the top Series A firms on the East Coast. So many firms have either left for the West Coast, or shifted their focus to earlier seed stage rounds or later stage rounds. There’s a real vacuum at the Series A funding and Sigma is filling it.

I also like their approach. All of my partners here are operators. We’ve backed some great companies, and we get behind our entrepreneurs and back them for their entire journey. We understand it takes time to build great companies. Startups are hard, and it usually takes longer than expected. I like how my partners stick with companies. It matches with my belief in perseverance and it pays off. For example, Sigma is an early investor in both Interactions and CloudHealth. Both companies are on fire, both just completed large follow-on rounds of financing, and their revenue growth is through the roof.  But it wasn’t always that way.  

I was at a point last summer where I was thinking about a $20M to 25M Oyster Angel Fund II. Then the Sigma opportunity arose. They thought my experience in customer acquisition and as an operator would be a good fit for joining their investment team. Since we already knew each other well, we knew it would be a good fit. 

I’m one year into it and I’m enjoying it. We are committed to Boston and the entrepreneurial ecosystem here. We are building one of the leading Series A Venture funds here in the city. I can’t think of a better place to be.

KC: What stage of investments do you primarily target and what is the current fund that you are investing from?

JD: We focus on Series A investments on the East Coast, and we’ll do a few selective seed rounds in the fund, but not often. We are currently investing out of Fund 9, and we have some great companies in the portfolio. Many of the companies are under the radar, names you don’t read about every day, but the traction and revenue growth we are seeing is very exciting.  

Doyle with family at the 2013 World Series

KC: What sectors of technology, industries, or trends are of interest to you?

JD: Our interests are pretty wide, as we look at anything that is technology enabled. In our Fund 9, 19 of our 21 investments are SaaS businesses. They have solid CAC/LVT ratios, strong sales productivity and low churn. That’s what we look for. Other areas of interest includes AI, cloud, infrastructure, marketing tools, robotics, security, and storage.  

KC: What are the top traits you look for in terms of investing into a company or founder?

JD: I look for great entrepreneurs who can see an opportunity and not give up. A great leader who can run through the wall and get their team to run through the wall after them. Perseverance is key too, as the founder needs to be patient and deal with the ups and downs. And obviously a founder that has a vision to go after something big, that isn’t necessarily obvious.

On my own personal website I talk about the 5Ps, which are all key: Passion, Patience, Persistence, Principles, and Pride. You can have a big market and strong technology, but the success of a company all comes down to the people and the 5Ps.

KC: How has the Boston ecosystem evolved over the years?

JD: So much has changed in favor of the entrepreneurs. Incubators and angels didn’t always exist. If you think about it, the ability to start a company is a lot easier than it has been previously. There is so much help and access to mentors. It’s a great time to be an entrepreneur in Boston.  

KC: What companies in Boston, outside of your portfolio, do you find interesting?

JD: So many companies are doing well right now. Obviously companies like Wayfair, HubSpot, and Acquia are doing some great things and are successful.

Drizly is a company that I’m rooting for, especially since they are BC grads. Drizly was raising their angel round before I was an investor, so I missed out, which is a bummer!

KC: Who do you consider as your mentors?

JD: I’ve had lots of great mentors who were lot of the people who invested in the Oyster Fund. They are all really smart people, who have run successful businesses.

So many people have helped me along the way. I don’t even know where to start. Ty Danco has been great and I appreciate how he opened my eyes to the startup scene in Boston. Paul Flanagan and all my partners at Sigma have all been super helpful. And of course, my parents played a huge role in shaping who I am.

KC: Can you tell us about the Edmund H. Shea Jr. Center for Entrepreneurship Center at Boston College that you’ve helped launch?

JD: I graduated from Boston College in 1987 and at that point in time, no one was doing anything entrepreneurial on campus. As I got entrenched in the Boston ecosystem, I saw what was going on at the other schools and was very excited when BC asked me to help accelerate the entrepreneurship program on campus. I love being involved with my alma mater, and helping students learn about what it takes to start or work at a startup is something I really love.

KC: Outside of being a VC, what are you personal interests or activities?

JD: I have four kids: three girls and a boy, and I’ve been together with my wife since my BC days... over 30 years! So a lot of what I do outside of work revolves around my family. I love traveling, because you can learn so much from other cultures. I also love golf, mainly because of the relationships you can build out on the course. And I’m also a huge walker. That’s another reason why I love Boston. It’s a great walking city, where I walk from meeting to meeting.

Keith Cline is the founder of VentureFizz. Follow him on Twitter: @kcline6.