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:

• Director of Partner Success and Strategy
• Executive Sales Operations Specialist
• Lead Fullstack Software Engineer
• Senior Partner Success Manager
• Senior Fullstack Engineer
• Product Manager, Data Platforms

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!