Senior Director, Inside Sales

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.

Role Requirements

• 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.

Total Rewards:

Additionally, we offer a comprehensive total rewards package, including but not limited to: medical, dental, vision, commuter benefits, a flexible time-off policy, paid parental leave, 401k match for US employees, wellness reimbursement, volunteering days, annual professional development budget, and charitable donation match.

Forward is proud to be a remote-first company, keeping workplace flexibility a top priority for our employees. As a business, we are focused on impact; we are more concerned with your contributions to the success of the company than where you get your work done. To help facilitate in-person collaboration, employees are welcome to work from one of our premiere office locations.

When we aren’t collaborating to drive business and support our customers, we’re finding virtual and in-person ways to get to know our colleagues, celebrate team wins, and have fun together!

Forward Financing Core Values:

• Drive the Mission - We believe in financial opportunity for underserved small businesses. We say “yes” when others say “no.”

• Keep It Real - We value direct communication, candid feedback, and authenticity. We are an open book.

• Act with Kindness - We create an environment where caring is cool and helping is the norm. We do the right thing.

• Shoot for Extraordinary - We are inspired by innovative thinking and continuous improvement.