Ready to launch your own podcast? Book a strategy call.
Frontlines.io | Where B2B Founders Talk GTM.
Strategic Communications Advisory For Visionary Founders
Conversation
Highlights
Welcome to another episode of Category Visionaries — the show that explores GTM stories from tech’s most innovative B2B founders. In today’s episode, we’re speaking with Will Sealy, CEO and Co-Founder at Summer, a student debt technology platform that has raised over $18 million in funding.
- Origins and Passion for Tackling Student Debt: Will started Summer to address the overwhelming challenge of student loan repayment affecting over 46 million borrowers saddled with $1.7 trillion in student debt. His personal and family experiences with student loans ignited his passion for this cause.
- Transition from Public Service to Entrepreneurship: Prior to founding Summer, Will worked on consumer financial protection and student loan issues at the newly established CFPB under the Obama administration, influenced by Elizabeth Warren. His government work laid the foundation for his entrepreneurial journey to solve the student debt crisis.
- Foundational Experiences and the Drive to Create Impact: Will’s earlier endeavor of starting a Safe Ride program during his college days showcased his natural inclination towards entrepreneurship and solving community issues, which later directed him towards addressing the larger societal problem of student debt.
- Admiration for Peer Entrepreneur: Will admires Jimmy Chen, CEO of Propel, for his mission-driven approach to using technology for social good, particularly in helping low-income Americans manage government benefits. This peer’s perseverance and successful product pivot deeply influenced Will.
- Business Model and Partnerships: Summer operates a B2C model, partnering with employers and financial institutions to offer a student debt management benefit to employees. This model encompasses planning for college costs, repaying student loans, and navigating tuition reimbursement programs.
- The Growing Crisis of Student Debt: Will highlighted the systemic issues leading to the student debt crisis, including rising tuition costs and the lack of financial literacy. He stresses the need for more substantial solutions beyond temporary debt relief measures to address the root causes.
- Future Vision for Summer: Looking ahead, Will envisions expanding Summer’s offerings beyond student debt management to include broader financial literacy and planning tools, aiming to solve adjacent consumer financial challenges and further empower individuals in their financial journeys.
- Importance of In-Person Engagement: Reflecting on personal experiences, Will values the power of in-person meetings for effective negotiation and relationship building, a principle he applies in various aspects of running Summer, from investor discussions to team recruitment.
Actionable
Takeaways
Leverage Your Expertise to Solve Complex Problems:
Will's deep dive into the student loan crisis during his tenure at the CFPB armed him with invaluable insights, emphasizing the advantage of building a startup in a domain where you possess profound knowledge. For founders, diving deep into a problem area can reveal unique opportunities for innovation and disruption.
Embrace a Mission-Driven Approach for Long-term Impact:
Will's passion for addressing the student debt crisis is a testament to the power of mission-driven entrepreneurship. Founders should identify causes they're genuinely passionate about, as this authentic commitment resonates with users, employees, and investors, driving sustained engagement and growth.
Take Charge on Educating Your Market:
Summer's focus on financial literacy underscores the importance of empowering consumers with knowledge to make informed decisions. B2B tech founders can explore opportunities to incorporate educational components into their solutions, enhancing user value and fostering trust.
Innovate in Distribution and Partnerships:
Summer's B2C model, utilizing partnerships with employers and financial institutions, highlights the importance of innovative distribution strategies. Founders should consider unconventional channels and partnerships to expand their reach and impact, tailoring approaches to fit the unique preferences of their target markets.
Value Face-to-Face Interactions for Key Negotiations:
Will's emphasis on the significance of in-person meetings, even in a predominantly remote work environment, illustrates the unmatched potential of direct interactions in building relationships and closing critical deals. Founders should not underestimate the power of personal engagement in pivotal moments, from fundraising to high-stakes negotiations.
Recommended Founder
Interviews
Andy Berman
CEO and Founder of Vowel
Andy Berman, CEO and Founder of Vowel: $13 Million Raised to Power the Future of Meetings
Jason Radisson
CEO and Founder of Movo
Jason Radisson, CEO and Founder of Movo: Over $9 Million Raised to Build the Future of HR Automation
Mike Fitzsimmons
CEO and Co-Founder of Crosschq
Mike Fitzsimmons, CEO & Co-Founder of Crosschq: $35 Million Raised to Power the Future of AI-Driven Hiring Intelligence
Michael Ioffe
CEO & Co-Founder of Arist
Michael Ioffe, CEO & Co-Founder of Arist: $16 Million Raised to Build the Future of Autonomous L&D
René Janssen
CEO and Founder of Lepaya
René Janssen, CEO & Founder of Lepaya: $85 Million Raised to Build the Future of Employee Training
Matt Pierce
CEO of Immediate
Matt Pierce, CEO of Immediate: $15 Million Raised to Eliminate the Costly Price of Financial Stress in the Workforce
Omer Glass
Co-Founder and CEO of GrowthSpace
Omer Glass, Co-Founder and CEO of GrowthSpace: $44 Million Raised to Build the Future of Employee Development
Nicole Fuselier
VP of Marketing of Bonusly
Revenue-Driven Marketing: Insights from Nicole Fuselier of Bonusly
Kian Katanforoosh
CEO & Founder of Workera
Kian Katanforoosh, CEO of Workera: $21 Million Raised to Build the Skills Intelligence Category
Agapitos Diakogiannis
Co-founder & CEO of Seafair
Agapitos Diakogiannis, CEO of Seafair: $6.5 Million Raised to Build the Future of Maritime Recruitment
Achuthanand Ravi
Founder & CEO of Kula
Achuthanand Ravi, CEO of Kula: $14 Million Raised to Build the Future of Recruiting
Virgile Raingeard
CEO of Figures
Virgile Raingeard, CEO of Figures: €8.5 Million Raised to Build the Future of Compensation Intelligence
Ian White
Founder of ChartHop
Ian White, Founder, CEO and CTO of ChartHop: $74 Million Raised to Build the Future of PeopleOps
Laura McGee
Founder and CEO of Diversio
Laura McGee, CEO of Diversio: $6 Million Raised to Help Organizations Measure and Improve DEI
Tony Jamous
CEO of Oyster
Tony Jamous, CEO of Oyster: $220+ Million Raised to Build the Global Employment Platform (GEP) Category
Sam Naficy
CEO of Prodoscore
Sam Naficy, CEO of Prodoscore: $4 Million Raised to Build the Future of Employee Productivity Measurement
Mousa Yassin
CEO and Founder of Pixaera
Mousa Yassin, CEO and Founder of Pixaera: $5.7 Million Raised to Build the Future of VR Safety Training
Hanns Aderhold
Founder and CEO of Cobrainer
Hanns Aderhold, Founder and CEO of Cobrainer: $21 Million Raised to Build the Future of Skills Data Platforms
Tuck Hauptfuhrer
CEO & Co-Founder of EarnBetter
Tuck Hauptfuhrer, CEO & Co-Founder of EarnBetter: $4.5 Million Raised to Build the Future of AI-Powered Job Search
Sid Upadhyay
Co-Founder & CEO of WizeHire
Sid Upadhyay, Co-Founder & CEO at WizeHire: Over $30 Million Raised to Help SMBs Hire Great Talent
Amit Bhatia
CEO & Co-Founder of Data People
Amit Bhatia, Co-Founder and CEO of Data People: $21 Million Raised to Build the Future of Recruiting Intelligence
Matthew Sydney
CEO & Founder of Beanstalk Benefits
Matthew Sydney, CEO & Founder of Beanstalk Benefits: $7.5 Million Raised to Build the Future of On-Demand Employee Benefits
Rob Whalen
CEO of PTO Exchange
Rob Whalen, CEO of PTO Exchange: $5M Raised to Empower Companies to Rethink Paid Time Off
Allen Narcisse
Founder & CEO of Gigs
Allen Narcisse, Founder & CEO of Gigs: $5.7 Million Raised to Build the Future of Blue Collar Hiring
Avi Singer
CEO & Founder of Showd.me
Avi Singer, CEO & Founder of Showd.me: $4.5 Million Raised to Build the Future of Compliance Training
Fraser Patterson
CEO and Founder of Skillit
Fraser Patterson, CEO and Founder of Skillit: $13 Million Raised to Tackle the Skilled Labor Crisis in Construction
Siadhal Magos
CEO & Co-Founder of Metaview
Siadhal Magos, CEO & Co-Founder of Metaview: $14 Million Raised to Power the Future of AI-Driven Hiring
Brett Martin
President and Co-Founder of Kumospace
Brett Martin, President and Co-Founder of Kumospace: $25 Million Raised to Power the Future of Virtual Offices
Nicholas Rudder
Co-Founder & CEO of Sphere
Nicholas Rudder, Co-Founder & CEO of Sphere: $5 Million Raised to Build the Future of Corporate Learning
Mike Adams
Co-Founder & CEO of Grain
Mike Adams, Co-Founder & CEO of Grain: $22 Million Raised to Power the Future of Meetings
Wes Winham Winler
Founder/CEO of Woven
Wes Winham Winler, CEO of Woven: $11 Million Raised to Transform How Companies Recruit and Hire Developers
Prem Kumar
CEO | Co-founder of Humanly
Prem Kumar, CEO of Humanly.io: $5.5 Million Raised to Build the Conversational Hiring Category
Joseph Fung
CEO of Uvaro
Joseph Fung, CEO of Uvaro: $15 Million Raised to Build the Career Success Platform Category
Anthony Mironov
CEO and Co-Founder of Wingspan
Anthony Mironov, CEO and Co-Founder of Wingspan: $30 Million Raised to Power the Contractor Experience of the Future
Josh Merrill
CEO of Confirm
Josh Merrill, CEO of Confirm: Over $11 Million Raised to End the Performance Review Nightmare
Nancy Xu
CEO & Founder of Moonhub
Nancy Xu, CEO & Founder of Moonhub: $10 Million Raised to Power the Future of AI-Driven Recruiting
Ben Sesser
CEO & Founder of BrightHire
Ben Sesser, CEO & Founder of BrightHire: $36 Million Raised to Build the Interview Intelligence Category
Matt Watson
CEO and Founder of Origin
Matt Watson, CEO and Founder of Origin: Over $70 Million Raised to Make Financial Wellness the Next Big Employee Perk
Albert Owusu-Asare
CEO & Co-Founder of Cadana
Albert Owusu-Asare, CEO & Co-Founder of Cadana: $7 Million Raised to Build the Future of Global Payroll Infrastructure
Raghu Gollamudi
CEO and Co-Founder of Included
Raghu Gollamudi, CEO and Co-Founder of Included: $5.4 Million Raised to Build the Future of HR Analytics
Karoli Hindriks
Founder of Jobbatical
Karoli Hindriks, Founder of Jobbatical: $23 Million Raised to Build the Future of Global Mobility with AI-Powered Relocation Solutions
John Kim
Co-Founder & CEO of Paraform
John Kim, Co-Founder & CEO of Paraform: $5 Million Raised to Build the Future of Recruiting with a Marketplace for Specialized Talent
Barbra Gago
CEO and Founder of Pando
Barbra Gago, CEO and Founder of Pando: $7 Million Raised to Build the Future of Career Advancement
Daniel Liebeskind
CEO and Co-Founder of Topia
Daniel Liebeskind, CEO and Co-Founder of Topia: $6 Million Raised to Help Organizations Build Their Own Metaverse
Sebastian Schüller
Co-founder of HiPeople
Sebastian Schüller, Co-founder of HiPeople: $7 Million Raised to Develop Data-Driven Augmentation for Hiring Teams
Kelsey Bishop
Founder and CEO of Candor
Kelsey Bishop, Founder and CEO of Candor: $5 Million Raised to Build the Future of Professional Relationship-Building
Stephen Johnston
CEO and Founder of GoodJob
Stephen Johnston, CEO and Founder of GoodJob: $9 Million Raised to Power the Future of Human Capital Management
Jennifer Dulski
CEO & Founder of Rising Team
Jennifer Dulski, CEO & Founder of Rising Team: $11 Million Raised to Build the Future of Team Performance
Tom Griffiths
CEO and Co-founder of Hone
Tom Griffiths, CEO of Hone: $50 Million Raised to Build the Future of Corporate Training
Carlos Gonzalez
Founder & CEO of Product School
Carlos Gonzalez de Villaumbrosia, Founder & CEO of Product School: $25 Million Raised to Power the Future of Product Management Education
Barb Hyman
CEO & Founder of Sapia AI
Barb Hyman, CEO & Founder of Sapia AI: $21 Million Raised to Build the Future of AI-Powered Recruiting
Sammy Singh
CEO and Co-Founder of WurkNow
Sammy Singh, CEO and Co-Founder of WurkNow: $15 Million Raised to Power the Future of Staffing
Chandler Malone
Founder of Bootup
Chandler Malone, Founder of Bootup: $2 Million Raised to Solve the Tech Talent Crisis
Hanna Asmussen
CEO and Co-Founder of Localyze
Hanna Asmussen, CEO and Co-Founder of Localyze: Over $48 Million Raised to Build the Leading Global Mobility Platform for Companies and Employees
Warren Lebovics
Co-Founder of Pequity
Warren Lebovics, Co-Founder of Pequity: $19 Million Raised to Build the Future of Employee Compensation
Marcelo Lebre
President of Remote
Marcelo Lebre, Co-founder & COO of Remote: Nearly $500 Million Raised to Power the Distributed Workforce of the Future
Ville Herva
CEO of BOLT.works
Ville Herva, CEO of BOLT.works: $7 Million Raised to Build the Future of Staffing
Jason Lavender
CEO of Electives
Jason Lavender, CEO of Electives: $10M Raised to Redefine Corporate Training
Jaclyn Chen
CEO of Benepass
Jaclyn Chen, CEO of Benepass: $14 Million Raised to Build the Future of Employee Benefits Management
Andres Blank
Co-founder & CEO of Fetcher
Andres Blank, CEO of Fetcher: $40 Million+ Raised to Build the Future of Recruiting Automation
Daniel Birkholm
Founder & CEO of TalentHub
Daniel Birkholm, TalentHub: $6 Million Raised to Transform How Organizations Measure and Improve Their Hiring Experience
Jared Pope
CEO and Co-Founder of Work Shield
Jared Pope, CEO and Co-Founder of Work Shield: $12 Million Raised to Eliminate Workplace Misconduct
Chris Johnson
Growth Marketing Lead of Gun.IO
Chris Johnson, Growth Marketing Lead at Gun.IO: Competing in the Future of Freelance Developer Marketplaces
Ben Zweig
CEO of Revelio Labs
Ben Zweig, CEO of Revelio Labs: $19 Million Raised to Build the Future of Workforce Intelligence
Nishika de Rosairo
CEO and Founder of HumanQ
Nishika de Rosairo, CEO and Founder of HumanQ: $3.5 Million Raised to Build the Future of Human Development
Peter Briffett
CEO and Co-Founder of Wagestream
Peter Briffett, CEO and Co-Founder of Wagestream: $370 Million Raised to Provide Financial Wellbeing for Every Frontline Employee
Kevin Busque
CEO and Founder of Guideline
Kevin Busque, CEO and Founder of Guideline: $339 Million Raised to Help More Small Businesses Offer Retirement Plans