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. We are not looking for a "caretaker" to keep the lights on. We are looking for an Inside Sales Architect—someone who wants to roll up their sleeves, reverse-engineer our conversion metrics and install a modern, data-driven outbound and renewal engine.

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

• Define what "good" looks like. Establish, monitor, and enforce critical daily inside sales baseline metrics (e.g., dial thresholds, talk-time targets, connection physics, and conversion throttles) across our 3 direct channels: New Sales, Renewals, and legacy Win-Backs (Paid-in-Full accounts).

• Serve as a dedicated mentor and execution coach to our 8 frontline sales managers. You will build internal leadership modules, running standard call calibrations and role-playing frameworks to elevate them from top-producing reps into highly analytical, structured leaders.

• Address current operational inefficiencies by restructuring how leads are routed, throttled, and assigned. You will ensure that our highest-converting closers maximize high-intent volume, rather than letting legacy account behaviors mask underlying conversion gaps.

• Act as the direct catalyst for integrating cutting-edge conversational AI and QA automation tools (e.g., real-time coaching interfaces, automated scorecard mapping) to transition the department away from manual, spreadsheet-based call scoring.

• Work in lockstep with our strict Underwriting and Risk teams. You will bridge the natural tension between sales velocity and credit box realities, coaching your managers to train reps to navigate complex objections seamlessly within non-prime underwriting guidelines.

Role Requirements

• High-Velocity Inside Sales Mastery: 4+ years of experience specifically leading short-cycle, high-volume transactional inside sales teams (1- to 5-day sales cycles, ideally with 1-touch or First-Call Close dynamics). You live, breathe, and sleep talk-time numbers and connection data.

• Multi-Layer Leadership Scale: 3+ years of experience directly managing managers within a structured, multi-layered inside sales hierarchy, overseeing an aggregate department of 50+ individual contributors.

• The "Ancillary / High-Objection" Excellence: Direct experience leading teams that sell high-objection, premium, or non-prime products where conversion requires absolute phone grit (e.g., alternative business funding/MCA, subprime consumer or auto finance, high-volume warranty/insurance extensions, direct-to-consumer home security).

• Turnaround Mindset: A proven track record of entering an under-managed or unstructured sales floor and successfully implementing performance management systems, scorecard transparency, and clear performance improvement plans (PIPs).

• Data Literacy over Intuition: The ability to look past raw team revenue numbers to uncover hidden inefficiencies, leverage CRM (Salesforce) data patterns, and restructure compensation multipliers to drive specific behavioral outcomes.