What are the responsibilities and job description for the Vice President of Sales position at Otterbrook?
About the Company
We are a fast-growing financial technology firm helping individuals and advisors build and protect wealth through modern tools and exceptional client experience. Backed by prominent growth investors and industry operators, our team combines deep expertise across wealth management, financial services, and technology.
The company has earned national recognition for innovation, client outcomes, and digital experience, and is led by an experienced executive team with more than two decades of leadership in financial services and technology startups.
Location: On-site, 5 days per week.
Reports to: Chief Executive Officer
Level: Vice President
About the Role – Vice President, Sales
We’re looking for a strategic and data-driven sales leader to own revenue growth across both consumer and enterprise business lines. You’ll lead a multi-channel sales organization—spanning direct-to-consumer, advisor partnerships, and enterprise distribution—and expand the team from roughly ten members today to more than twenty within the next year.
This position requires an experienced executive who has successfully scaled multi-motion sales operations into the eight-figure ARR range. The ideal candidate can execute in the short term while designing scalable systems for the long term.
Key Responsibilities
- Own revenue strategy and execution: Set direction for all sales initiatives across multiple business units, including forecasting, pipeline management, and sales operations.
- Scale the organization: Architect and grow the sales function—developing processes, compensation models, and enablement programs that drive predictable, efficient growth.
- Build and coach teams: Recruit, develop, and manage high-performing sales, business development, and account management teams.
- Drive adoption and retention: Partner closely with Marketing and Product to ensure lead quality and conversion align with growth targets.
- Leverage data and systems: Implement CRM discipline, data frameworks, and reporting dashboards that turn insights into measurable performance improvements.
- Collaborate cross-functionally: Work closely with senior leadership in Product, Marketing, Finance, and Operations to align GTM strategy, pricing, and client experience.
- Lead by example: Foster a culture of accountability, urgency, and ownership across the revenue organization.
About You
- Proven ability to coach, inspire, and elevate performance standards across a growing team.
- A structured operator who scales growth through repeatable systems, not one-off heroics.
- Experienced in building and expanding multi-product, high-growth sales organizations.
- Skilled at balancing strategy and execution in complex go-to-market environments.
Experience
- 10–15 years of experience selling to financial advisors, RIAs, or related wealth-management firms—ideally within fintech, asset management, custody, or digital-investment platforms.
- Demonstrated success driving and scaling eight-figure annual revenues while leading multiple sales motions.
- Deep understanding of GTM metrics (CAC/LTV, pipeline velocity, sales efficiency).
- Strong analytical mindset with a bias toward measurable results.
Benefits
- Comprehensive medical, dental, and vision coverage.
- Retirement plan with employer match.
- Commuter and wellness benefits.
- 20 days PTO annually.
- Regular team meals and cultural events.
- Opportunity to influence company direction as part of a rapidly scaling leadership team.