Group Program Manager, Enterprise PMO

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.

The Group Program Manager - Enterprise PMO is the senior practitioner at the top of the Enterprise PMO, responsible for the intake, governance, reporting, dependency, and capacity discipline the function needs to be a genuine strategic partner to the business.

You will work directly with the VP Product and lead the PMO team. You will own the things that require judgment, experience, and credibility across functions, and you will develop the next generation of PMO talent beneath you.

In This Role You Will:

• Design and own how the PMO runs, including intake, governance frameworks, tooling, and reporting standards. Define the business case standard every initiative must meet before it earns a slot in the portfolio, and hold that standard when senior stakeholders push against it. Ensure Product and PMO operate from a shared system of record to build a model that scales with the business.

• Own portfolio reporting and a single source of truth that leadership can act on. Treat data quality as a first-order problem so that no team maintains a parallel spreadsheet alongside the system of record.

• Surface systemic execution and delivery risk across Engineering, Credit, Fraud, Analytics, Sales, and Marketing early and cross-functionally with a proposed action plan. Build the delivery risk cadence for the PMO from the ground up and identify patterns before they become problems. Own cross-functional dependency management, mapping what each initiative needs from whom before commitments are made rather than after dates slip.

• Partner with Product, Engineering, and Analytics to build the forward-looking initiative roadmap each quarter. Facilitate the sequencing conversation and frame trade-offs with a commercial lens rather than just a capacity lens, ensuring the PMO has a strong voice in what gets built, in what order, and why.

• Own quarterly resource planning as well as the cross-portfolio resource view across Engineering and Analytics to surface capacity conflicts and bottlenecks before they become delivery risks. Partner directly with Engineering and Analytics leadership without intermediaries.

• Own the steering committee and portfolio review cadence, ensuring the right decision reaches the right forum at the right time and that leadership has an honest picture of portfolio health, including where it is unflattering.

• Own initiative-level budget tracking and benefits realization across the portfolio, measuring whether initiatives delivered what their business case claimed and feeding that back into intake. Partner with Finance on portfolio-level spend visibility, and produce the cost, benefits, and risk inputs behind the monthly portfolio narrative the VP Product delivers to the CEO and directs.

• Manage and develop the project managers directly by coaching on delivery craft, risk framing, and stakeholder communication. Create a visible development path for the PMO team so everyone moves up a rank as the business grows, building a proactive team environment.

• Leverage AI to automate Product Operations workstreams around timeline mapping, risk identification, sequencing, task assignment etc.

Requirements:

• (Even if you don’t check every box, but see yourself contributing, please apply.)

• 10+ years in program or portfolio management, with at least 3 years operating at a senior level in fintech, financial services, or a similarly complex environment.

• Demonstrated experience owning the commercial narrative for a portfolio, with a proven track record of building the "so what" story for a C-suite rather than just a status report.

• Deep fluency in delivery risk identification across multiple business functions, showing an ability to catch systemic patterns before they turn into major problems.

• Proven executive presence with the ability to be comfortable, credible, and commanding in the room with a CTO, CFO, or capital markets partner.

• Experience designing, building, or rebuilding a PMO operating model, intake frameworks, governance, and reporting standards in a growth-stage organization.

• Strong financial acumen, including budget ownership, cost of delay, and ROI framing as part of your natural vocabulary.

• A proven track record of developing talent, managing senior practitioners, and creating clear growth paths to make the team proactive and successful.

• Lending, payments, or a broader financial services background is strongly preferred to effectively hold commercial conversations about the business. (preferred)

Compensation:
Annual Salary: $187,000 - $256,000 CAD
Annual Bonus: You have the potential to earn an additional 15% annual bonus.

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!

Our Culture: The Forward Compass

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.