Head of Programme Management

About the Role
We are looking for a hybrid Program Manager who lives at the intersection of traditional program delivery, AI operationalization, and Agile coaching. This highly collaborative, hands‑on role will act as a change agent across our engineering, product, and design org.

One week you may be managing high‑level cross‑functional timelines; the next, you’ll embed directly into a development team to help them smoothly adopt new delivery workflows and tighten their Scrum practices. The role is all about strategic execution and ensuring the product development engine runs smoothly.

A massive part of your initial impact will involve leading our migration away from legacy knowledge bases into modern, AI‑optimized documentation hubs. You will architect our documentation so internal AI agents and LLM orchestration tools can pull flawless context from it, now and in the future. You’ll also have the opportunity to redesign our product analytics usage in Pendo and ensure we’re maximizing the tools available to our customers.

Responsibilities
1. Product Discoverability & Knowledge Architecture

Lead end‑to‑end migration and architectural overhaul of our user‑facing documentation from legacy platforms to modern, developer‑friendly documentation hubs.

Architect technical documentation to be optimized for semantic search and Retrieval‑Augmented Generation, ensuring internal and external AI agents pull flawless, highly accurate context.

Redesign our product analytics and in‑product guide implementation to deploy impactful, context‑aware in‑product guides and walkthroughs that maximize immediate value and self‑service help for our users.

2. PM‑Eng Connective Tissue & Agile Delivery

Audit, declutter, and structurally organize our sprawling internal Confluence space across Product, Design, and Engineering, establishing strict governance, fresh templates, and self‑updating best practices.

Embed directly into engineering and product squads as a hands‑on coach to audit and optimize their adherence to agile practices, helping them tighten their SDLC delivery loops.

Champion our product delivery infrastructure, ensuring teams maintain an aggressive, highly transparent, and organized feature pipeline.

Proactively hunt down and eliminate legacy, bureaucratic processes. Design lightweight, high‑velocity playbooks that keep cross‑functional teams executing at AI speed.

Own the operational drumbeat of the department by planning, coordinating, and executing high‑impact R&D All‑Hands meetings and leadership off‑sites.

3. Metrics & Adoption Tracking

Leverage product analytics and internal telemetry to build robust analytical frameworks that track feature adoption, user drop‑off points, and overall platform health.

Apply the 5 Whys methodology to product usage data, digging past surface‑level metrics to deliver deep behavioral insights that product managers can immediately turn into actionable feature optimizations.

Track team delivery velocity and execution health, stepping in to help teams manage risks and raise flags early if a critical launch timeline is jeopardized.

4. GTM (Go‑To‑Market) Interface

Build and run a tight, predictable communication rhythm between R&D and Go‑To‑Market teams to ensure total company alignment on upcoming releases.

Work cross‑functionally to ensure GTM teams can seamlessly leverage our customer‑facing help tools, making it effortless for support and customer success to unblock users and scale adoption.

5. R&D Programs & Cross‑Functional Delivery

Drive high‑visibility, cross‑functional R&D programs, ruthlessly managing complex, cross‑team timelines, resource bottlenecks, and technical dependencies.

Coordinate the operational readiness for big product initiatives, ensuring Product, Design, Engineering, and Ops are completely lockstep as new capabilities transition from early versions to live, enterprise‑ready production.

Bring a high‑agency, “get‑it‑done” mentality to massive initiatives, eliminating administrative drag and steering critical corporate priorities across the finish line.

Cross‑Cutting AI Automation
Across all five pillars, you will build and maintain lightweight AI automation workflows that eliminate repetitive ops work, from documentation maintenance to status reporting to dependency tracking. This is not a separate workstream; it is how you operate.

Qualifications

5+ years of experience managing complex technical programs, software delivery, process design, operationalizing programs, product/engineering operations, or consulting within a fast‑paced technology or SaaS environment.

Solid experience migrating or managing documentation away from legacy systems. Knowledge of how LLMs consume data and hands‑on exposure to collaborative AI tools (Claude, Gemini) and AI workflow automation platforms.

Experience migrating documentation from legacy systems into modern platforms and building lightweight automation workflows using AI tooling.

Deep experience leveraging product analytics (Pendo or comparable platform) to optimize digital adoption. Ability to apply the 5 Whys methodology for root‑cause analysis.

Track record of auditing, cleaning up, and organizing sprawling internal resource sites, establishing lasting documentation governance and eliminating legacy processes.

Exceptional communication skills. Comfortable engaging in productive, data‑driven conflict and saying difficult things directly while receiving feedback with curiosity.

First‑principles problem‑solving mindset, thriving in ambiguity and managing multiple moving parts under tight timelines.

Education
Bachelor’s degree required; Master’s preferred. Areas of study include Business, Process Improvement, Operations, Technology Management, and related fields.

Location
This is a remote‑first role. Candidates must be based within roughly a 2‑hour drive of major metro areas in the United States and be willing to travel occasionally for business purposes.

Salary, Benefits, & Perks

Flexible Time Off

Paid Holidays - 16 U.S. paid holidays, including a winter break.

Health Benefits - medical, dental, and vision coverage with multiple plan options. Fertility assistance included.

Retirement - 401(k) plan through Fidelity with a company match up to 4%.

Stock Options - all employees share in company success through stock options.

Mental Health Program - well‑being support through SpringHealth program.

Paid Family Leave - up to 12 weeks of 100% paid leave for baby bonding, adoption, and caring for family members.

Paid Medical Leave - up to 12 weeks of 100% paid leave for childbirth and medical needs.

InVacation - a bonus after 7 years of service.

Wellness Subsidy - subsidy for gym memberships, fitness classes, and more.

Position Base Range - $94,000-$114,000 per year plus bonus.

DEI Statement
We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or expression, or veteran status. We are proud to be an equal‑opportunity workplace.

#J-18808-Ljbffr Bonfirevc