Frontline Strategist (Product Manager), FDE

WorkWhile•San Francisco, CA

5d•Remote

About The Position

WorkWhile is building a category-defining Frontline Deployed Engineering (FDE) pod. This world-class team is focused on going deep with key enterprise customers, understanding their operational reality, and building solutions that make WorkWhile genuinely work for them. The ultimate goal is to compress time to PMF-at-scale for key accounts and compound learnings across the portfolio. As the first Frontline Strategist (Product Manager), you will be the connective tissue of this pod. You will work directly alongside Frontline Engineers and customers to define what gets built, why, and in what order, translating messy field problems into clear product direction. You will report to the Head of Product and work closely with the CEO on the vision for this motion.

Requirements

7+ years in a product management, technical program management, or highly consultative customer-facing role.
“Founder Mode” at the core: you can articulate a big vision, demonstrate high agency, speak truth with conviction, you are resilient and always put the team and mission first.
Track record of working directly with external customers or clients, not just internal stakeholders, to define and deliver solutions.
Comfort operating in ambiguity: you've scoped work from incomplete briefs before and know how to move forward anyway.
Strong written and verbal communication; you can hold a room with a VP of Operations and a conversation with an engineer in the same afternoon.
Instinct for prioritization: you know the difference between what a customer is asking for and what they actually need.

Responsibilities

Customer-facing: Embed with enterprise customers alongside Frontline Engineers, understanding their workflows, their data, their constraints, and where WorkWhile fits (and where it doesn't yet).
Lead discovery and scoping conversations with customer stakeholders, often without a fully defined brief.
Own the feedback loop from the field: synthesize what you're seeing across customers into patterns, and surface those patterns as product signal.
Product & Roadmap: Define and prioritize what the FDE pod builds — custom integrations, workflow tooling, customer-specific extensions — in collaboration with engineering and the core product team.
Make clear calls on build vs. configure vs. escalate: know when a customer problem is a one-off and when it's a product gap.
Drive rapid prototyping cycles with the FDE team: get something in front of customers fast, learn from it, and iterate.
Partner with core product stakeholders to ensure field learnings influence the roadmap, not just the backlog.
Pod Operations: Establish the operating rhythm for the FDE pod: how engagements are scoped, handed off, tracked, and closed.
Keep cross-functional stakeholders (GTM, Customer Support, Operations) aligned on what the pod is doing and why.
Help build the playbook from scratch: this pod will be a reference model for how WorkWhile scales enterprise delivery.