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.
We are seeking a Senior Customer Engagement Representative who is focused on winning back previous clients with a paid in full balance and re-engaging them as clients. We are looking for a "Top 1%" performer who is motivated by metrics and obsessed with conversion. You will be responsible for re-engaging our successfully graduated merchants, turning "Paid In Full" status into new funding opportunities through sheer volume, strategic follow-up, and technical precision.
Act as a Consultant: Speak with business owners to assess goals, address questions, and present renewal options
Drive the Dialer: Master a high-volume auto-dialer environment, maintaining the stamina to deliver high-quality pitches on the 100th call of the day as effectively as the 1st.
Salesforce Execution: Use Salesforce as a tactical weapon. You will be expected to manage high-velocity lead queues, ensuring that every record is updated in real time to reflect the current funnel stage.
Collaborate: Work with internal teams to support timely and accurate funding outcomes, including Sales, Processing, Underwriting, Collections, and Accounting.
Act as a Mentor: Ability to support and mentor more junior reps through daily processes and initiatives.
Performance Optimization: Constantly analyze your own performance data. If your conversion dips, you are expected to diagnose the "why" (e.g., call timing, script delivery, or lead source) and pivot immediately.
Beta Tech & Documentation: As a Senior rep, you will pilot new tech (dialer enhancements, AI logging, etc.) and provide concise, actionable feedback.
Your success is measured by hard data. We expect the following:
Activity Volume: Consistent daily attainment of outbound call volume, talk time, and multi-channel touchpoints (SMS/Email).
Conversion Efficiency: Maintaining a high lead-to-opportunity and opportunity-to-funding percentage.
Quota Attainment: Monthly and quarterly revenue targets are treated as a floor, not a ceiling.
Funnel Management: Zero "leaks" in the pipeline; 100% of assigned PIF leads must be touched within strict SLAs.
The Experience: 1+ years of experience in a sales environment
The Mindset: You are competitive and metric-driven. You enjoy seeing your name at the top of the leaderboard and are motivated by hitting stretch goals.
Technical Command: 1+ years experience updating deals daily in a CRM (Salesforce preferred)
Comfort with hustle metrics: Comfortable with high phone activity in a fast-paced environment, familiarity with auto-dialer, strong time management, strong organization habits, Able to request, review, and communicate clearly about financial documents
Resilience: High comfort level with "no" and the ability to pivot to a "yes" through consultative selling and persistence.
Annual Targeted Salary: $50,000 – $60,000 CAD
Monthly Variable: You have the potential to earn an additional $2,000 CAD per month in variable compensation. The final payout of variable compensation is determined by achievement of performance metrics.
At Forward Financing, we're committed to fair and transparent compensation. We believe in providing a compensation package that recognizes your skills, experience, and the unique value you bring to our team. We take a market-based approach to pay, regularly reviewing benchmark data to ensure our compensation remains competitive, equitable, and aligned with our performance-driven culture.
Final offers are determined by a variety of factors, including the candidate's qualifications, relevant experience, specific skills, and internal equity. This approach ensures that our compensation is competitive and equitable. Your recruiter will provide specific details on the expected base and variable earnings as it pertains to this specific role. This position is to fill an existing vacancy.
Total Rewards:
Additionally, we offer a comprehensive total rewards package, including but not limited to: medical, dental, vision, a flexible time-off policy, paid parental leave, RRSP match, 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!
The Forward Compass is the standard we hold for ourselves and one another—guiding how we lead, collaborate, and show up every day to move in the same direction.
Back the Builders: We are wired to fuel customer progress, not just provide support.
Rooted in People: We create an environment that balances deep connection with the extreme ownership and honesty required to reach our highest potential.
Flying V: We move through coordinated effort with speed and urgency to achieve what no individual could do alone.
Always Forward, Never Finished: We pursue growth with a relentless drive that keeps us ahead of the competition.
About Us:
Forward Financing is a fintech 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. Whether facing challenges accessing traditional financing or simply needing a convenient, flexible solution, Forward is committed to funding more of the millions of small businesses nationwide. By simplifying the requirements, streamlining the process, and using advanced proprietary technology, Forward is often able to deliver approvals within hours and funds that same day – giving more businesses the financial opportunity they need to thrive. Plus, with their dedicated teams and award-winning service, customers get personalized support when they need it most.
Since 2012, Forward has expanded access to capital by providing over $4.8 billion in funding to more than 92,000 small businesses. The company is A+ rated by the Better Business Bureau with an Excellent / 4.7 stars rating on Trustpilot.com. Recognized as a Best Place to Work by Built In Boston and certified as a Great Place To Work, Forward is dedicated to empowering both its team and the customers they serve, helping them succeed and thrive.
Equal Opportunity Employment Information
It is the policy of Forward Financing to ensure equal employment opportunity without discrimination or harassment on the basis of race, religion, national origin, status, age, sex, sexual orientation, gender identity or expression, marital or domestic/civil partnership status, disability, veteran status, genetic information, or any other basis protected by law. We welcome and encourage applications from people with disabilities. Please let us know should you require any accommodations. As part of our commitment to a streamlined and equitable hiring experience, we use AI tools to assist with candidate screening and assessment.
