Technical Program Manager - Customer Success

Flatfile is full of builders driven by a dual desire to make cool stuff and create tangible value. We pride ourselves in obsessing over the details, but also grounding our decision-making and pace in whether we’re doing what’s in the best interest of our end users.

This is a highly strategic role operating at the core of Flatfile project delivery and customer success. You’ll act as the primary program lead for our customers, orchestrating complex project planning, coordinating cross-functional resources, and ensuring the successful execution of data exchange solutions. Success in this role demands exceptional organizational skills, a strong technical foundation, and the ability to translate evolving requirements into actionable, high-impact project plans.

This role reports to: VP of Customer Success

Flatfile is a post–product-market fit AI company with rapidly accelerating growth, tons of runway, and a lean, hungry, and sharp team playing for a huge outcome.

We’re closing enterprise deals and evolving our platform quickly to meet growing demand. As we take on increasingly complex, high-value customer projects, the need for an experienced, hands-on Technical Program Manager to ensure precise planning, clear communication, and smooth execution has never been more critical.

We have an ambitious roadmap ahead of us, and we’re looking for someone eager to lead these customer-impacting initiatives from kickoff to success.

• Collaborate directly with enterprise and mid-market customers and internal/external technical teams to design and deliver solutions to complex data exchange challenges

• Own project scope, timelines, and milestones - tracking progress, managing dependencies, and ensuring on-time delivery

• Build customer-facing training documentation, conduct testing, and become a Flatfile product expert

• Provide regular, clear project status updates to both the customer and internal stakeholders

• Facilitate effective communication between product, engineering, and customer-facing teams to align priorities and deliverables

• Identify and navigate organizational bottlenecks, mitigating risks and escalating issues as needed

• Maintain thorough, organized documentation of project processes, decisions, and changes

• Contribute to the continuous improvement of project management methodologies and tools, sharing best practices across the team

• Proven experience as a Program Manager, Project Manager, or similar role in a software development environment

• Experience with technical products and a strong understanding of software development processes, methodologies, and lifecycle management

• Excellent written and verbal communication skills, with the ability to articulate technical and project concepts to varied audiences

• Strong organizational skills and the ability to manage multiple priorities simultaneously

• Hands-on experience with project management tools such as Jira, Trello, Asana, or similar

• A collaborative mindset and the ability to thrive in a fast-paced, dynamic startup environment

• Strong problem-solving skills and meticulous attention to detail

• You prefer to stay removed from technical discussions and aren’t comfortable navigating both business and engineering conversations

• You are uncomfortable managing competing priorities and shifting timelines in a rapidly evolving product landscape

• You shy away from influencing diverse stakeholders or facilitating cross-functional alignment

• You prefer a highly structured environment with minimal ambiguity; this role requires adaptability and independent problem-solving

• You’ve never worked in a fast-paced environment. We move quickly, and if you get frustrated when priorities change rapidly, we’re not the place for you

Compensation Range: $150K - $170K