Director of Enterprise Sales

About Middesk

Middesk makes it easier for businesses to work together. Since 2018, we’ve been transforming business identity verification, replacing slow, manual processes with seamless access to complete, up-to-date data. Our platform helps companies across industries confidently verify business identities, onboard customers faster, and reduce risk at every stage of the customer lifecycle.

Middesk came out of Y Combinator, is backed by Sequoia Capital and Accel Partners, and was recently named to Forbes Fintech 50 List and cited as an industry leader in business verification by digital identity strategy firm, Liminal.

The role

As the Director of Enterprise Sales at Middesk, you’ll lead a team of high-performing enterprise account executives and take ownership of driving revenue growth. Your mission will be to develop and implement strategic sales initiatives that create long-term value for our customers, while building a team culture centered on coaching, accountability, and excellence.

You’ll collaborate with Marketing to design pipeline-generation programs and identify expansion opportunities, and partner with Finance to ensure that forecasts are data-driven and aligned with Middesk’s overall goals. You’ll also work cross-functionally with Product and Account Management to shape the product roadmap and refine our go-to-market strategy, ensuring that we’re consistently exceeding customer expectations.

Above all, you’ll foster a team that enterprise sellers aspire to join—a high-impact team known for its ability to navigate complex customer landscapes and unlock strategic growth.

We follow a hybrid work model, and for this role, there is an expectation of 2 days per week in our SF or NYC office. Candidates should be based within a commutable distance, as we believe in the value of in-person collaboration and building strong team connections while also supporting flexibility where possible.

What You’ll Do

• Hire, onboard, and mentor a team of six to eight enterprise account executives, ensuring they’re consistently exceeding performance goals.

• Coach individual AEs on deal strategy, leveraging your deep understanding of the financial services sector to help them close and expand relationships with top banks, fintechs, and financial services partners.

• Develop and execute strategic pipeline-generation initiatives that drive both new business and land-and-expand growth within existing accounts.

• Shape the team’s approach to multi-threading and influence mapping, ensuring we’re engaging at the most senior levels within customer organizations.

• Build a robust framework for identifying new use cases and expanding Middesk’s presence within large, complex customer environments.

• Foster a culture of accountability, collaboration, and continuous improvement, with a focus on coaching and upskilling team members to help them grow into future leaders.

• Set clear performance goals for your team and manage progress through structured reviews, ensuring we’re always aligned on outcomes and moving quickly to address gaps.

• Deliver accurate, data-driven revenue forecasts on a rolling two-quarter basis, partnering closely with Finance to ensure predictability and alignment with Middesk’s broader revenue goals.

• Collaborate across the business—working with Product, Account Management, and Marketing to refine our GTM strategy and inform the product roadmap based on customer feedback and market insights.

What We’re Looking For:

• 5+ years of experience leading and managing teams of Enterprise Account Executives

• Proven success in hiring, onboarding, and developing talent in a high-growth environment.

• Demonstrated success in working with the top 50 banks, large fintechs, equipment finance companies, and fast growth tech customers, including managing complex relationships, influencing and negotiating at senior levels, and driving land-and-expand sales motions.

• Experience thriving in earlier-stage, high-growth companies—bringing both strategic vision and tactical execution to unlock new customer segments and accelerate revenue.

• Experience in selling technical solutions with a usage/volume-based model, and the ability to engage with customers on technical topics.

• Proven ability to use data to accurately forecast results, identify upsell and cross-sell opportunities, and drive business outcomes.

• Extensive experience collaborating closely with account management, product, and marketing teams to enhance customer engagement and drive growth.

 Nice to Haves:

• Experience with data, identity, or risk products: Familiarity with products related to data, identity, or risk, and an understanding of their unique customer needs.