Senior Director, Strategic Finance - Go-To-Market (GTM)

Toast • Boston, MA

30d

About The Position

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy. The Strategic Finance team turns data into insight—and insight into impact. We partner across the company to translate performance metrics into strategic decisions that accelerate growth, efficiency, and long-term value. We’re seeking a Senior Director of Strategic Finance to partner with our Go-to-Market (GTM) organization, including our Chief Revenue Officer (CRO) and Chief Marketing Officer (CMO). This leader will shape growth strategy and inform capital allocation decisions across Sales, Marketing, and Onboarding to drive sustainable ROI. You’ll lead a talented finance team that loves solving complex problems and collaborating with operators across the business. This is a high-impact, visible role reporting into a VP of Finance that blends strategic influence with hands-on execution.

Requirements

• 15+ years in Strategic Finance, FP&A, or related fields, within SaaS, Fintech, or high-growth tech.
• Proven success leading GTM or Revenue Finance teams and driving accountability to public-company standards.
• Deep understanding of SaaS metrics (CAC, LTV, payback, churn, expansion, ARR, retention) and growth levers.
• Strategic, analytical, and comfortable operating in dynamic, fast-paced environments - enjoys balancing detail with big-picture vision.
• Proven leadership in guiding, mentoring, and scaling high-performing teams to achieve ambitious goals in a growth-focused organization.
• Executive communicator able to influence C-suite leaders and drive alignment.

Responsibilities

• Strategic Business Partnership: Advise the CRO & CMO on turning business vision into actionable financial strategies.
• Leadership: Lead and develop a high-performing GTM Finance team while serving as one of the senior leaders within the broader Finance & Strategy organization.
• Planning & Forecasting: Own target-setting and forecasting for bookings and GTM expense planning; drive the long-range plan and annual budget cycles.
• Analytics & Insights: Provide clear visibility into funnel metrics, sales productivity, CAC, LTV, and payback to inform strategy and improve ROI.
• Investment Frameworks: Prioritize GTM investments, headcount, and spend to maximize growth and efficiency.
• Pricing & Retention Strategy: Partner with Marketing and Product to evolve monetization, deal desk, & retention models that strengthen revenue and lifetime value.
• Business Reviews: Partner with leadership on monthly and quarterly business reviews, highlighting opportunities for acceleration or course correction.
• Systems & Process Excellence: I mprove forecasting models, automation, and dashboards to enable faster, smarter decisions.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed
• Number of Employees: 5,001-10,000 employees