MGMT Boston - W6, Q4 24 - Clasp / Brian Mongeau, Caveonix
Clasp / Brian Mongeau, Caveonix / The Lantern
Welcome to MGMT Boston where we try to help 1,070+ of you manage your awareness of top Boston startups and local up & coming operators putting in the work. Glad to have you here!
TLDR:
Clasp - a mission-driven, venture-backed fintech startup tackling critical talent shortages by bridging the gap between education and employment
Thanks to Matt Davis for the intro to Clasp
Brian Mongeau, VP Operations at Caveonix - a servant, soldier, operator, and leader who’s invested his time (and dollars) into leading teams with a bias to action in a multitude of demanding environments across the globe
The Lantern Last Week: Andrew Lau, Jellyfish / Will Lehmann, Step Function Ventures
Other Resources:
MGMT Boston Operators Club - a community and opportunity engine for 90+ Boston based up & coming venture backed operators
The Lantern Short Form Video Series (YT) - Intro Trailer / Simon Taylor, HYCU / Nathan Rosenberg & Marc Printz, Farmblox / Jenni Goodman, Underscore / Jason Lavender, Electives / Daniel Pelaez, Cyvl / Sean Smith, Denim / Palash Soni, Goldcast / Andy Palmer, Entrepreneur & Investor / The Market is Getting Better
2024 Boston Tech Big Board - 2024 Companies to Watch (evolving list)
The Endeca Effect: Overview / Markets / People / Products / Conclusion / Bonus - Steve Papa Alumni Learnings
Q4 Operators Highlighted: Laura Andre / Qunett, Dana Louie / InvoiceCloud, Sarah Clarkson / Vestmark
2023 1H Recap / 2023 2H Recap / 2024 Q1 Recap / 2024 Q2 Recap / 2024 Q3 Recap
Clasp
Founder: Tess Michaels
Founding: 2018
Mission: Revolutionize the way employers attract and retain critical talent in hard-to-hire fields—while simultaneously tackling the student debt crisis.
Employees: 45 & 50%+ Local
Workplace: Hybrid
Stage & Capital Raised: Series A+ & $30M raised
Investors: Crosslink Capital, Firework Ventures, GSV Ventures, Slow Ventures, Sinai Ventures, SHRM
Key Customers: Warby Parker, MyEyeDr., General Assembly, Galvanize
Glassdoor Rating: 4.4
Valuation (estimated): $75M (assuming average equity dilution in the $10M 2024 Series A+ fundraise)
^ this is a useless number from MGMT Boston. There is no tangible valuation until the business is sold or goes public. Don’t forget it!
Clasp is a mission-driven, venture-backed fintech startup tackling critical talent shortages by bridging the gap between education and employment. By enabling employers to invest in future talent where it matters most—easing overwhelming student debt—Clasp’s platform creates lasting bonds between employers and employees.
In 2018, Tess Michaels was frustrated. As she progressed through her MBA studies at Harvard Business School, she had come to the conclusion that not only was higher education expensive, the borrowing process was less than consumer friendly, and there were a ton of inequities in terms of who could access higher education. Why were some students forced to bear more of a burden to get a great education?
Having begun her career in investment banking and then private equity, she understood the rails of capitalism and how someone might be able to build bridges for skilled students who weren’t previously able to cross them.
In June of 2024, 43M+ Americans held federal student loan debt and the collective balance exceeded $1.7T. Student loans are the second largest category of consumer debt behind mortgages (src). It’s a major asset class!
Clasp, fka Stride Funding, was founded to offer Income Share Agreements (ISAs) to students in high-outcomes programs with repayment terms based on post graduation income. The Clasp team got very good at underwriting debt and building the fintech infrastructure needed to handle loan servicing at scale. David Kafafian, a law student who also experienced this asset class that wasn’t working very well for consumers, soon joined as COO to help take the business to the next level.
In 2022, with a national network of schools and programs, and over 10,000+ students on its fintech platform, the Clasp team evolved to realize an even bigger vision: helping turn student loans from a liability into an asset for employers and talented graduates alike.
Today, Clasp matches employers with workforce shortages and students with student loan debt to not only recruit student talent earlier, but help pay off their student loans over a specified retention period once they join full time. That’s a win-win.
Some industries in particular, like healthcare, are really struggling to acquire talent. There are 4.3M registered nurses working in our healthcare system, but an annual shortage of almost 200k projected between 2020 and 2023 (src). Educational institutions alone can’t handle the volume of educating the number of professionals needed to fill this widening gap.
Enter Clasp. Using their fintech expertise, employers will onboard Clasp’s end-to-end student talent acquisition and retention platform to extend a standout offer: an upfront career commitment and student loan repayment benefits after hire.Their team helps employers optimize their acquisition of highly skilled labor for specialty positions in trades like nursing, optometry, veterinary, and more, while replacing incentives like sign-on bonuses and reducing cost of recruiting and turnover for a significant ROI. Clasp has already added dozens of supported employers since they began acquiring Enterprise healthcare clients about 18 months ago.
From their previous ISA focused product line, they have built direct to student channels and established a powerful network of higher education relationships after previously graduating hundreds of candidates from these schools on their platform each year going back 6+ years. Clasp has supported 10,000 students in their borrowing journeys to date, with $175M of student loan assets currently on the platform. In addition to their own access-driven private education loans, the Clasp platform can remit payments to more than 100 federal and private loan servicers. Between their existing school relationships and employer recruiting teams, Clasp supplements the distribution that their customer’s recruiters can reach. Their team supports the talent engagement, matching, and then the repayment and/or borrowing experience to help talent be “Day 1” ready.
Working principally with CHROs and Finance teams, they are facilitating smoother employee acquisition and retention with the numbers to back it up. Their team has internal data which shows that every $1 invested through Clasp returns up to $3-$4 in savings by replacing signing bonuses and lowering employee turnover costs.
Clasp has reached seven figures in ARR and is planning to grow their enterprise footprint significantly as they continue this exciting new direction heading into 2025.
The team has grown to almost 50 FTEs, with 30 based in Boston, including their entire engineering, product, partner success, finance & marketing orgs. Sales, naturally, spans the coasts. With Tess founding Clasp while at Harvard Business School in Boston and David & their CTO, Andrew Kenney, based here in Boston, it has become a natural HQ for the company’s growth as they’ve added a number of local headcount this year and plan to continue growing in Boston in 2025.
Operators to Know:
Rachelle Fecteau, Director of People
Scott Russian, VP of Finance
Renée Mang, VP of Operations
Karoline Andris, Chief Compliance Officer
Graham Opie, Director of Operations & Program Management
Morgan Viehman, Director of Brand & Marketing
Harsh Rana, Data Engineering & Analytics Manager
Kevin Toomey, Senior Manager, Product
Carissa Zukowski, Senior Manager, Engineering and Data
My investigative powers continue to need work so apologies to the Stride team if I missed any up & coming operators internally
Key Roles To Be Hired:
If I were interviewing here are some questions I’d ask:
What are the key milestones Clasp needs to achieve to continue its progress toward this new enterprise focused platform shift?
What are Clasp’s core employer and geographic markets?
What are the biggest challenges as you scale the team past 50 employees?
What is the long term vision for the company?
What are the most important roles you’ll be looking to add in 2025 // teams that need the most help?
We’re optimizing for readability here so to learn more about Clasp you’ll have to D.Y.O.R. I’m excited to watch this team bring more employers and talented graduates into professional alignment. All lenders & borrowers applaud your efforts. See you around town!
Brian Mongeau, VP Operations @ Caveonix
Brian Mongeau is a servant, soldier, operator, and leader who’s invested his time (and dollars) into leading teams with a bias to action in a multitude of demanding environments across the globe. Today he is the VP of Operations at growth stage cybersecurity company Caveonix.
Growing up locally alongside his younger brother, Brian served as an officer in his high school’s debate club, editor-in-chief of the school newspaper, played sports, and became an Eagle Scout, laying the foundation for a career in service. His dad taught him that “things are earned, not given” and his mom helped him see the world in a different way with her approach to leading a spiritual and balanced lifestyle. Growing up in the shadow of 9/11, Brian was inspired to give back and serve in our nation’s military. A high school teacher and later college professor helped provide the mentorship for him to decide it was the right path.
He studied History, Political Science, and International Relations with concentrations in Southeast Asia, American foreign policy, and global security at the University of Wisconsin. As graduation neared, he was slicing turkey sandwiches at Jimmy John’s by day and bouncing at a bar aptly named the Nitty Gritty by night in Madison as he awaited his formal enlistment to the Army.
He chose to enlist instead of pursuing officer training because this path would lead him more quickly to the elite Special Forces groups. Two years later, Brian finished his qualifications to become a Green Beret.
Over seven years, he was deployed 7 times between Afghanistan and the Asia-Pacific region. The world was shifting during his career in service as Asia’s economies emerged and that concentration in Southeastern history was put to good use!
He worked on a small team of 12 operatives who trained and operated alongside partner armed forces across the world. Their job required building rapport, navigating ambiguity, and bridging cultural differences. Through his work Brian learned to find the best in people and develop trust alongside a small team that always needed to move quickly.
After seven years he left the Army to begin a three year joint program between Harvard’s Kennedy School and Harvard Business School to obtain his MBA and MPP. It was a chaotic transition to civilian life, Brian admits, which took him some time to reacclimate.
Before classes commenced, he interned at Goldman Sachs’ Veterans Integration Program, quickly learning how much he didn’t know…about what he didn’t know.. reintegrating back into society. Their back office Operations program helped him realize that a career in investment banking, with the hours and time away from family much like a military career, was not going to be the best fit for him as he sought to restart his career in his 30s.
Settling into his Cambridge studies, he loved hopping between the Kennedy School & HBS over those three years. He made a lot of close friends in his section (Section G!), benefited from tremendous faculty mentorship, and pivoted his skills and mentality to adjust to what he would need to succeed in the private sector.
During his second year, he interned in the Office of Congressman Seth Moulton, to test out a career in government service. Then he transitioned to CrowdStrike for 18 months on a part time basis as the world went remote with Covid. Brian was put in the right place at the right time as his team stood up a new business unit that went from $0 to $200M ARR. His first daughter was born during this time and he got to spend a lot of formative time with her at home after many years out in the field.
CrowdStrike was a foundational experience where he had great leaders (Jen Ayers, Todd Crosley, Jessica Alexander) overseeing him, just like in the military, who taught him a lot about high growth business building. One week before graduation, as the pandemic waned, Brian took a role at logistics tech startup Convoy through a HBS connection. His family planned to move back to Seattle (where he had previously been stationed) and Convoy was scaling up their Growth team to develop a new business line during a hypergrowth phase.
But because of the pandemic they never ended up making the move and another opportunity surfaced, through a connection from HBS with a fellow Army vet (Josh Lospinoso), to join cybersecurity & defense focused venture capital firm First In. Brian helped the team close their first fund, establish a brand, and prove themselves. They closed the fund right as the War in Ukraine began and the industries of cybersecurity, national security, and defense were being elevated to first order problems to be solved. Reflecting his passion for innovation in partnerships between the public and private sectors, Brian was additionally named a 2022 Aspen Strategy Group Rising Leader and Council on Foreign Relations term member during this time.
Caveonix is a portfolio company of First In and, when the company brought in some operating resources to help the company reposition, Brian jumped at the chance to become an operator again. Alongside First In Operating Partner Aloysius Boyle, who had joined as Caveonix’s CEO, Brian came onboard to add operational rigor and level up his leadership skills in an early stage environment.
Brian is responsible for executing strategic initiatives & handling leadership responsibilities at the management team’s table across Sales Operations, Customer Success, Solutions Architecture, and Partnerships. The first 10 months were a whirlwind as they made a lot of changes to establish a new culture & operating rhythm. Now, they’re running one of the best GTM teams Brian has ever worked with, made up of some previously overlooked operators, who want to build something great.
He manages cross functional efforts for strategic projects and Caveonix is on pace for triple-figure growth in 2024. Through honing their product focus and staying committed to serving customers, they are headed toward a new phase of accelerating growth. The conversations are fundamentally different and a whole lot of fun!
Both Brian and his wife are from the Boston area and want to grow their careers & lives here. It’s the tight sense of community, smart people, and even “slight edge” that Boston residents have that’s tough to beat. As Brian says, it “helps hone your instincts!”
Chaos & Ambiguity = Opportunity
In the Special Forces, Brian went through a lot of tense situations. Ever the statesman, he likes to say that chaos and ambiguity present opportunities. He’s been trained for it!
As he’s transitioned to the startup world, he has learned that many people are worried about change and chaos. But Brian insists that his experiences have taught him that these situations are opportunities to learn and provide a chance to demonstrate your abilities in a way that can be transformative.
“Why do we love David Ortiz? In 2004 he hit home runs when things were not going well. He wanted to be up at the plate with the opportunity to compete for his team and do something special, even if he was probabilistically likely to fail.”
Chaos can present the best times to advance in your career & move faster. In the “crucible”, you learn the most about yourself.
During his time in the Army, they had a process for navigating rapid change. First, they encouraged their operators to take a tactical pause, look around, and get their bearings. Basically, rapidly figure out your “context & stakeholder mapping” before taking your first step. Then when you do take a few steps, stop and ask yourself “is this working / making sense?”. Respond, iterate, and do it again.
In the Army they would do “AARs” (after action reviews) to talk about what occurred in the field where they would call out the facts of the mission’s events. Then they would suggest “3 improves” and “3 sustains” to prioritize structure and also limit takeaways to prevent beating themselves up over extensive mistakes.
If you can slow things down in a chaotic environment and develop a deliberate learning cycle through processing your learnings, in military and civilian environments, you can go far!
3 Career Insights / Learnings
Maintaining Learning Mentality - “The best people I know, who consistently impress and who I’ve tried to emulate, are the people who put learning front & center every day with a sense of humility”
Hone Your Strengths, Lean on Team - “I used to think that not being well rounded was a weakness. In the Army I wasn’t good at lifting weights but I could get from point A to point B pretty well. I’ve learned that being effective is about honing your strengths and building a well rounded team that can fill in each other’s gaps”
Have a Bias for Action - “It’s better to have an 80% solution acted upon than waiting for a 100% solution. You can always iterate & improve if at the very least you’re in the game and moving forward. If you wait, you might miss opportunities”
Brian is on a path to becoming an accomplished executive, continuing to learn the startup ropes operate after navigating all different types of challenging environments. The operating world needs more leaders who can grow companies, individuals, & teams and Brian is committed to helping lead people & &people lead in mission driven organizations. He’s also seeking the elusive balance between his personal and professional life to find an equilibrium. Amen to that, Brian.
If you want to learn more about Brian you can find him spending time with his family on the South Shore, building GTM & Operations teams at growth stage companies, or on LinkedIn. Thanks for sharing. We’re excited to see all of the teams & leaders you inspire here in Boston and beyond over the coming decade!
The Lantern: Andrew Lau, Jellyfish / Will Lehmann, Step Function Ventures
Last week on The Lantern..
Andrew Lau shares what’s happening at Jellyfish this fall, how engineering management is about solving business problems, and how getting involved will help grow your career:
Will Lehmann tells us about his work at Step Function Ventures, investing in the best technical founders, and his journey to starting his own fund (plus check out his newsletter demystifying VC > In Lehmann’s Terms):
The Lantern - a short form video series by MGMT Boston featuring the best startups (+founders), ecosystem leaders, and ferociously talented operators in Boston
W9: Andrew Lau, Jellyfish / Will Lehmann, Step Function Ventures
W8: Palash Soni, Goldcast / Andy Palmer, Entrepreneur & Investor / The Market is Getting Better
W7: Daniel Pelaez, Cyvl / Sean Smith, Denim
W6: Jenni Goodman, Underscore / Jason Lavender, Electives / Productize Yourself
W5: Simon Taylor, HYCU / Nathan Rosenberg & Marc Printz, Farmblox
W4: Remen Okoruwa, Propexo / Amelia Van Camp, Mirakl
W3: Alex Ewing, OneScreen / Jess Lynch, FoundersEdge / What is MGMT Boston? And Why?
W2: Aniketh Mohanty, Wayfair / Amber Nigam, Basys.ai / W2 Summary (The Agents are Coming)
W1: Trailer Launch / Markit AI / W1 Summary (Setting the Culture)
Any feedback for me? One thing you liked? One thing you didn’t? Local startups or operators to highlight? Just reply to this e-mail!
See you next week!
-Matt