Forward Financing is a financial technology company based in Boston, Massachusetts with team members throughout the United States, Dominican Republic, and Canada. The company is on a mission to unlock the capital that fuels small businesses across America. Recognized as a Best Place to Work by Built In Boston and certified as a Great Place To Work®, Forward is investing in its employees, technology, and customer experience – with long-term success in mind every step of the way.
As the Sr. Director of Inside Sales, you will lead a high-performing organization of 70+ employees, including 8 managers. Reporting directly to the Chief Revenue Officer (CRO), you will own the strategy and execution for three critical channels: Direct-to-Merchant New Sales, Renewals, and Win-Backs. Your mission is to drive sales excellence, foster a high-octane culture, and scale our internal talent to meet the demands of a fast-growing fintech environment.
Why Join Forward?We are building a world-class fintech company where long-term success is prioritized at every step. If you are a builder who thrives in a fast-paced, highly transactional environment (1-day sales cycles) with a passion for developing talent, we want to hear from you.
Even if you don’t check every box but see yourself contributing to our mission, we encourage you to apply.
In this role you will
Drive the strategy for direct sales channels to consistently exceed revenue targets and long-term growth KPIs.
Partner with the CRO on sales forecasting, company-wide initiatives, and real-time performance analysis.
Act as a lead architect for departmental change, ensuring seamless implementation of new processes while maintaining high team buy-in.
Leverage analytics to assess individual and departmental performance, evolve sales processes, and design competitive compensation programs.
Partner with Sales Ops, Underwriting, and Marketing to launch new campaigns and optimize the customer journey.
Collaborate with the Technology team to build and refine tools that drive rep efficiency and automation.
Build a world-class sales environment through rigorous performance management, mentorship, and continuous training.
Focus on developing the next generation of sales leaders at both the front-line and mid-management levels.
Proven Leadership: 8+ years of sales experience, with at least 3 years managing managers.
High-Volume Expertise: 4+ years of experience in short-cycle, high-volume inside sales management.
Departmental Ownership: 3+ years of experience overseeing a full department or business unit with P&L or heavy quota accountability.
Education: Bachelor’s Degree required; MBA preferred.
Analytical Rigor: Ability to quickly digest complex data sets and translate them into actionable sales strategies.
Industry Background: Experience in financial services or fintech is a significant asset.
Communication: Exceptional verbal and written skills with the ability to influence at the executive level.
Skills Required
- 8+ years of sales experience
- 3 years managing managers
- 4+ years in high-volume inside sales management
- 3+ years overseeing a department with P&L accountability
- Bachelor's Degree
- MBA preferred
- Analytical skills to digest complex data
- Experience in financial services or fintech
What the Team is Saying
Forward Financing Compensation & Benefits Highlights
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Healthcare Strength — Comprehensive medical, dental, vision, and mental‑health coverage is emphasized, with added supports like an EAP. Life and disability insurance further reinforce the core safety net.
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Leave & Time Off Breadth — Open/unlimited PTO is paired with paid holidays, sick time, floating holidays, birthdays off, bereavement, volunteer days, and paid parental leave. This breadth signals flexibility for rest, family needs, and community engagement.
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Wellbeing & Lifestyle Benefits — A monthly stipend usable for wellness, commuting, or home‑office needs, plus fitness support and occasional gym access, extend value beyond insurance. Onsite perks and commuter benefits add everyday convenience for office‑based staff.
Forward Financing Insights
What We Do
Forward Financing is a financial technology company based in Boston, Massachusetts with team members throughout the United States, Dominican Republic, and Canada. The company is on a mission to unlock the capital that fuels small businesses across America. Forward has been recognized as a Best Place to Work by Built In and is certified as a Great Place To Work.® We’re investing in our employees, technology, and customer experience – with long-term success in mind every step of the way. Want to learn more? Visit: forwardfinancing.com/careers
Why Work With Us
We’re building a place where our people want to run to work every day. Here, you’ll be with colleagues who work together towards shared goals and challenge you to bring your best; you’ll work with leaders who support your professional growth and want to see you succeed.
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Forward Financing Offices
Remote Workspace
Employees work remotely.
Our Employee Choice policy allows most team members to choose if they’d like to be fully remote, work in our Boston headquarters, the office in the DR, or a hybrid combination.
