• Zach Servideo

074: Boston Speaks Up with Entrepreneur Dan Rossignol

Updated: Jun 19

Boston Speaks Up (BSU) is a podcast owned and operated by Value Creation Labs. Listen to BSU on any podcast platform you choose: SoundCloud, Spotify, Apple Podcasts, Stitcher, and Google Play.


Dan Rossignol is an entrepreneur, investor and lifelong learner with a proven track record as a technology generalist who can drive revenue across business verticals. He currently serves as the Chief Growth Officer at Stonehenge Technology Labs, doing business as STOPWATCH, a Bentonville, Arkansas-based unified commerce software startup that provides real-time supply chain management for global CPG brands.


Rossignol is also a scout investor for Bonfire Ventures, a seed stage venture capital firm that leads Seed rounds for business software solutions company founders.


Prior to his current roles at STOPWATCH and Bonfire Ventures, Rossignol was in multiple leadership positions from co-founding Ad On Feet, an experiential guerilla marketing company, to serving as the Head of Partnerships at UserTesting ($USER), where he built and ran the company’s first channel sales and strategic partnership playbook across all of their strategic consulting and digital agency partnership networks.


Having led business development, product marketing, and operation teams across the globe, Rossignol has a unique humanity-first approach to operating and investing. From startups to scale ups, he leverages several years of operating experiences to help underestimated teams build a better future for tomorrow, today.


You can listen to our podcast discussion embedded below or on any podcast platform you prefer (SoundCloud, Spotify, Apple Podcasts, Stitcher, and Google Play):

Pre-Podcast Q&A


Where did you grow up? And how would you describe your childhood?


Born in Haiti, later adopted and grew up in Central Maine, Middle Class near Colby College. Very conservative and multi-cultural home. Mom was a school teacher at a small private school called Temple Academy. Dad worked for the states largest power company for over 30 years.



Who were your role models growing up?


Athletes and my grandfather were my role models. I was fairly gifted in both Lacrosse and Football (soccer). My grandfather was the first businessman I had ever been exposed to and he was a very successful New York Life Insurance salesman. He later went on to own dry cleaning businesses and other random enterprises. I lost him my junior year of high school and was pretty shook.


What is the first career you remember wanting to pursue?


I wanted to be a lawyer because all of the people in a small town that had money were lawyers, doctors, or accountants. I headed down that path in college and quickly realized that I was better suited for a path towards early stage ventures.


To help out our younger listeners tuning into the show, can you speak on your internship experience(s)? In addition, can you share any insights you may have on the importance of internships/experiential learning (outside the textbook)?


I’ve had several internships but the most memorable was with a company called Brightspark Ventures a Pre-seed and Seed stage VC based in Toronto ON. That experience exposed me to how venture works and what is required to be venture backable. At BS I worked on iStopOver.com one of the first competitors to AirBNB in the early days of “marketplaces” which now it seems everyone has one or wants to be one.


What’s your advice to young people breaking into the tech startup scene?

My advice is to not seek to enter into the startup scene on purpose, but rather seek to identify problems in which you feel you would be uniquely qualified to address and hopefully solve. Too many people are mid-guided on what the purpose of a startup is these days. IMHO it’s when a project that people or a sole individual is working on becomes too large and requires teams, innovation, capital, partnerships in order to arrive at solving a problem at scale.


Is there a particular person or event that helped shape the career path you took?


My uncle Paul has been my greatest lighthouse as I have come up in my career. He has been there to support me and give me guidance 100 steps before I get to a particular cross-road. He has been a Fortune 500 C-suite executive and now spends his time as a Boston based Venture Capitalist in the Life Science space. He has been very critical to my development.


As far as events I think having started my first venture in college I was pretty destined to keep hacking at startups and the adjacent world that supports their existence.


What is the biggest challenge you’ve overcome getting to where you are today?


Well the mere fact that I am here today is the biggest challenge. I was adopted out of Haiti in which I was not well suited to survive having been taken to an orphanage as a young child. I am blessed to have all that I have.


Speaking on the topic of leadership, and seeing that you’ve held MANY leadership roles throughout your career thus far, what’s the biggest lesson you’ve learned from your experiences leading others thus far?


The easiest day was yesterday - US Navy Seals.


How would you describe your leadership style?

I subscribe to - You can go faster alone, but further together - US Army.

We are in a team sport at all times and must understand that each of us play a critical role in each other's wins and losses.


What’s the most exciting part about the tech startup sector?


The Omni-Commerce space is really exciting these days which is why I have made recent investments in companies supporting the global digital transformation legacy brands and retailers are going through.


I also love doing deals in places like Bentonville AR, home to Walmart. The talent is amazing and the cost to start and operate a business is extremely favorable compared to the east/west coast regions.


Have you noticed any big differences between the current states of the startup sectors in Boston vs Providence?


I think given the close proximity there aren’t too many differences. That said valuation comps are different and the rate of growth are for sure different. Boston startups tend to grow faster. I don’t have data on that, it's just a hunch.


What do you find most exciting about being an entrepreneur? (Not limited to just starting a company, but rather being entrepreneurial in the way you work/think)


That change is the only consistency. I need to be doing different things each day that are deliberately aligned to getting to smart goals or OKR’s. I love organized chaos and enjoy seeing the different types of people come in and out of startups.


What sorts of challenges and opportunities have you found in the pivot to virtual business and networking during the COVID-19 pandemic?


Obvious one for me as a leader is that it's hard to stay organically connected to my team after we hang up a Zoom or Teams call. We miss the “swivel chair” crunch sessions where we can quickly ask each other for help or physically high five our wins and losses.


That said, we are now tuned towards optimizing our time together to ensure we maximize what is important and where we need to INFORM or DECIDE on critically important topics.


What are some of the most recent trends you’ve been seeing in the startup scene? What do you believe will succeed in longevity?


Huge valuations and too many companies. Not seeing very many bold and pioneering ideas. Lots of formula based go-to-markets. I think pattern recognition is driving the startup scene at large, which sucks.


FINAL QUESTION: We like the idea of ending our episodes with a challenge for the listeners/readers. Whether it be reaching out to an old friend, reading 5 pages a day from a book, creating a new healthy habit… What is one challenge you have for the listeners?


I challenge the listeners to take inventory of their ideas and be honest about which ones are opportunistic and which ones are aspirational. Pick the aspirational ones to tackle because those will involve a lot of hardship and challenges. We need to solve more problems that require deep thought, slow/fast execution, and most importantly outsized value to the down market customers or users.


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You can follow BSU on Twitter at @BostonSpeaksUp, and recommend BSU guests by contacting bostonspeaksup@gmail.com.

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