Head of Strategic Sales

SentiLink; Chicago (IL); Hybrid; USD 450,000 - 550,000; Full time

Benefits offered by this job

Employer paid group health insurance

401(k) plan with employer match

Flexible paid time off

Regular company-wide in-person events

Home office stipend

Job summary

SentiLink is seeking a Head of Strategic Sales to lead and scale enterprise opportunities across new markets in the United States. You will identify, develop, and close multi-stakeholder deals, partnering with product, marketing, and leadership to shape go-to-market strategy.

The role emphasizes consultative selling, executive engagement with Fortune 500 and high-growth clients, and building repeatable sales motions to extend lighthouse successes. Remote-friendly, US-based role.

Qualifications

• 10+ years of enterprise software sales experience.
• Proven success closing high six to seven figure deals.
• Experience selling into financial services, fintech, fraud, or identity.
• Proven experience developing go-to-market strategies and expanding into new markets.

Responsibilities

• Lead, coach, and scale SentiLink's Strategic Sales team to win major enterprise opportunities.
• Develop and execute go-to-market strategies for new industries and buyer personas.
• Recruit, hire, and onboard top sales talent as the team grows.
• Identify and win flagship customers to establish credibility in new verticals.
• Build executive relationships with C-suite and senior leaders across Fortune 500 firms.
• Lead complex enterprise sales cycles from initial engagement to contract execution.

Skills

Enterprise sales

Strategic deals

Executive relationship building

Go-to-market strategy

Team leadership

Job description

SentiLink provides innovative identity and risk solutions, empowering institutions and individuals to transact with confidence. We’re building the future of identity verification in the United States replacing a clunky, ineffective, and expensive status quo with solutions that are 10x faster, smarter, and more accurate.

We’ve seen tremendous traction and are growing extremely quickly. Our real-time APIs have helped verify hundreds of millions of identities, starting with financial services and rapidly expanding into new markets. SentiLink is backed by world-class investors including Craft Ventures, Andreessen Horowitz, NYCA, and Max Levchin.

We’ve earned recognition from TechCrunch, CNBC, Bloomberg, Forbes, Business Insider, PYMNTS, American Banker, LendIt, and have been named to the Forbes Fintech 50. We have also been named a 2026 FICO Industry Vanguard Decision Award Winner. Last but not least, we’ve even made history - we were the first company to go live with the eCBSV and testified before the United States House of Representatives on the future of identity.

SentiLink supports a variety of ways to work, ranging from fully remote to in-office. We operate as a digital-first company with strong collaboration across the U.S. and India. We maintain physical offices in Austin, San Francisco, New York City, Seattle, Los Angeles, and Chicago in the U.S., and in Gurugram (Delhi) and Bengaluru in India. If you’re located near one of these offices, we would love for you to spend time in the office regularly. Some roles are hybrid or in-office by design. For example, our engineering team in India works primarily from our Gurugram office.

Role

As Head of Strategic Sales, you will lead and scale SentiLink's efforts to win large, strategic enterprise customers and expand into new markets beyond our traditional financial services customer base. You will identify, develop, and close complex, multi-stakeholder opportunities that establish SentiLink as the leading identity and fraud platform across new industries.

This role is ideal for a highly consultative strategic sales leader who enjoys opening new markets, navigating complex organizations, and partnering closely with executive buyers to solve mission-critical business problems. While experience selling into financial institutions is highly valuable, we're equally interested in leaders who have successfully introduced infrastructure or risk products into new enterprise verticals.

Reporting to the Chief Revenue Officer, you'll work closely with Product, Marketing, Partnerships, and Executive Leadership to shape go-to-market strategy, influence product direction through customer feedback, and scale our strategic sales motion as SentiLink enters its next phase of growth.

This is a remote-friendly, US-based role.

Responsibilities

• Lead, coach, and develop SentiLinks Strategic Sales team which delivers the largest and most strategic enterprise sales opportunities.
• Develop and execute go-to-market strategies for new strategic industries, buyer personas, and strategic product initiatives.
• Recruit, hire, and onboard exceptional talent as the team continues to grow.
• Identify and win flagship customers that establish credibility in new verticals.
• Possess and build executive relationships with C-suite and senior business leaders across Fortune 500 and high-growth enterprise organizations.
• Lead complex, multi-stakeholder enterprise sales cycles from initial engagement through contract execution.
• Develop compelling executive narratives that connect SentiLink's fraud and identity capabilities to customer business priorities.
• Partner closely with Product to influence roadmap priorities based on strategic customer needs.
• Work with Marketing to evolve messaging, positioning, and customer stories for new markets.
• Collaborate with Partnerships to unlock strategic distribution opportunities.
• Help develop repeatable sales motions that can scale beyond initial lighthouse customers.
• Represent SentiLink at executive briefings, conferences, and industry events.

Requirements

• 10+ years of enterprise software sales experience, including significant experience leading large, strategic enterprise deals.
• Demonstrated success selling complex platform or infrastructure solutions with contract values typically in the high six to seven figures.
• Experience selling into financial services, fintech, fraud, identity, risk, or adjacent infrastructure markets is strongly preferred.
• Experience recruiting, coaching, and developing top-performing enterprise sales talent.
• Proven experience developing go-to-market strategies and expanding into new markets, industries, or enterprise segments.
• Experience selling into industries such as marketplaces, healthcare, insurance, gaming, telecommunications, or other large enterprise verticals is also highly valued.
• Alternatively, experience successfully selling enterprise infrastructure, security, compliance, data, or workflow platforms into new industries.
• Experience leading complex enterprise sales cycles ranging from 6–18 months, navigating multi-stakeholder buying committees to consistently close high-value strategic partnerships.
• Exceptional consultative selling, negotiation, and executive communication skills.
• Strong product curiosity and ability to translate customer problems into product opportunities.
• Experience partnering closely with Product, Marketing, and Executive Leadership to drive company wide outcomes.
• Comfortable operating in ambiguous, high-growth startup environments.

Compensation

• $450,000-$550,000 OTE + equity + benefits

Perks

• Employer paid group health insurance for you and your dependents
• 401(k) plan with employer match (or equivalent for non US-based roles)
• Flexible paid time off
• Regular company-wide in-person events
• Home office stipend, and more!

Corporate Values

• Follow Through
• Deep Understanding
• Whatever It Takes
• Do Something Smart