About Me
Hi! My name is Jason Cianchette and I grew up here in Portland, Maine. Went to school in Boston at Tufts where I met my wife and studied computer engineering. I received my MBA from Dartmouth and worked for a number of venture-backed startups focused on data, marketing, and technology.
In 2008, I started a mobile marketing company. We offered customers a turnkey solution of ad buying, website development, and analytics all using outcomes based pricing. The company grew quickly and I sold it to Publishers Clearinghouse in 2011. That exit was my first real lesson in what it feels like to build something and hand it over to a buyer, which gives me a lot of empathy for sellers and founders that I work with today.
In 2017, I bought the business that became Marketshare. Its core product, AskGMS, analyzes sales data from 24 leading insurance carriers in order to provide market intelligence. The business built a second product called Benefeature, which combines public data sets like employee benefit plans, LinkedIn data, Glassdoor, and insurance licensure data to create a distribution intelligence tool for carriers and brokers. We're SOC 2 certified because we handle sensitive customer data, and we take that seriously.
I live in Cumberland, Maine, with my wife and our three kids. When I'm not working, I'm usually out on Casco Bay fishing, on a golf course, or at a kid's soccer or lacrosse game.
Liquid Wireless
Founded in 2008, Liquid Wireless pioneered mobile-optimized direct marketing. We built great technology and an even better team — with a high-performing and fun culture that was named one of the Best Places to Work in Maine. Publishers Clearing House acquired the business in 2011, where the team continued to grow and innovate.
AskGMS
Acquired in 2017 from its founder, AskGMS is a cornerstone in market intelligence for group insurance carriers. We adopted a four-day work week and became a remote-first team. The team has seen zero employee turnover in four years, a testament to our focus on work-life balance and employee satisfaction.
Benefeature
Launched in 2022, Benefeature is a new product developed by the AskGMS team. They saw an opportunity in the market to develop a new SaaS-based sales tool for insurance carriers and have received significant resources and room to explore this concept.
What Kind of Businesses Does Retego Acquire?
I'm looking to acquire one or two more businesses over the next few years — established, profitable companies where I can be a good long-term owner and where my background is actually useful.
Paid search, paid social, programmatic, technical SEO, CRO. I'm a data and numbers guy. I understand how to make a campaign perform and evaluate the performance. Giving a Don Draper–style presentation about how things feel — that's not me.
HubSpot, Salesforce, Klaviyo partner ecosystems. I'm very confident that for AI agents or any automation to really work, you need very structured customer data. A CRM is one of the most logical places for that to grow from.
Marketing intelligence, benchmarking platforms, compliance automation, business intelligence. Marketshare is the clearest example: it looks like a professional services company, but its moat is twenty years of proprietary insurance data.
The through-line is what I think of as a "data asset dressed as a services company" — operational substance, proprietary data workflows, and technology leverage, but valued as a running business rather than at inflated SaaS multiples.
Size. I'm targeting businesses with $500K–$2M in EBITDA or SDE for standalone platforms, and I'll look at smaller bolt-ons in the $300K–$800K range when the strategic fit is clear. Revenue typically falls in the $1.5M–$5M+ range.
What I look for
- 75%+ recurring or retainer-based revenue
- 60%+ gross margins
- 20+ active clients, average tenure over 18 months, no single client over 12–15% of revenue
- A strong internal leader or GM who can run daily operations post-close
- A moat that AI can't easily replicate: client trust, system integrations, workflow complexity, or proprietary data
What tends to not be a fit
- Extreme founder-dependence — the founder is the sole rainmaker, sole client contact, and sole technical operator
- High customer churn (above 20–25% annually) or high team turnover
- High customer concentration
- Financials that require significant unwinding to understand
- Sellers who are "exploring the market" without a clear reason to sell
How I Think About AI and Technology
I've been a tech guy for almost 30 years, and I don't believe AI is about to replace everyone. Instead I prefer the Iron Man suit approach: how do you make an employee a lot more efficient, help them skip the drudgery, give them access to better information? Usage hasn't caught up with capability yet. There's a tremendous runway in front of us.
I find efficiency gains from AI less interesting than the new things it makes possible.
- Removing friction from creative workflows.
- Giving teams access to intelligence and insights they couldn't get otherwise.
- Finding what's slowing people down and allowing them to just be their best selves.
Why Work With Me
I've been on your side of this. I founded a company, built it with a team, and sold it. I know that what a purchase agreement captures and what you're actually handing over are two very different things — the relationships, the institutional knowledge, the culture that keeps good people from leaving, the dozens of small decisions that never show up in a financial model.
I have a lot of respect for founders. I want to maintain their legacy and build on it. If a company has a good name, strong customer relationships, and a culture that works, my instinct is to protect those things and improve selectively around the edges.
The people matter to me. When I look at a business, one of the first things I'm evaluating is how long the core team has been with the company and if they'll stay with the company under new ownership.
On deal structure
I don't need to raise capital, get committee approval, or consult with investors. I have the money available and can move as quickly as I need to.
I'm experienced with SBA expansion financing, conventional debt, seller notes, Section 338(h)(10) elections, and F reorganizations — whatever structure makes sense for the specific situation.
Frequently Asked Questions
Why are you buying businesses instead of starting them?
Starting companies is really hard. I've done it, and I respect how hard it is. But I realized I'm more effective when I can take something that already works — real customers, real data, real team — and make it better. I like building systems, not buildings.
What's your involvement after you buy a company?
It depends on what's most useful. With Marketshare, I was hands-on for about four years, then transitioned day-to-day operations to my operating partner. Ideally, I'm closer to full-time when I acquire something new — especially in the first year. I like to understand how things work. But I'm flexible about what my role looks like. What matters to me is contributing to the best of my ability.
Will you keep the existing team?
That's the plan. The team is usually the main reason I'm interested in a business in the first place. I'm not buying a company to cut heads. I'm looking for businesses where the team is strong and where my background — technology, product, data, marketing — fills a gap the current team doesn't have.
How do you feel about remote teams?
Very comfortable. Marketshare is fully remote. I've managed remote teams of 50 people in the past.
What industry experience do you have?
My deepest expertise is in marketing technology and data analytics. I've built lead gen platforms, loyalty marketing systems, and B2B intelligence products. I have nine years of experience operating in the insurance and financial services industries through Marketshare. I'm also experienced with regulated industries, data security (SOC 2), and enterprise sales cycles.
How quickly can you close?
I can move as quickly as I need to. All capital is personal — no fundraising, no committee, no bank approval required for the equity portion.
What's Retego?
Retego is the holding company I use to acquire and operate businesses. It's just me — not a fund, not a platform. The name comes from Latin, meaning "to uncover." It reflects how I think about finding and revealing the value in businesses that are already doing great work.
Let's Talk
The businesses I find most interesting are often the ones most people have never heard of: a company serving a specific corner of an industry it knows cold, with customers who've been there for years and an owner who's ready to hand it to someone who will take care of it.
If you're a seller thinking about what comes next — or a broker with a client who fits what I've described — please contact me.
hello@retego.co