Frontline Strategist , FDE

What you’ll do

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

What we’re looking for

• 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

Benefits & Perks

• Competitive base salary + equity in a high-growth, venture-backed company
• Remote work culture with hybrid opportunities in SF, NY, Seattle & Toronto
• In-person company offsites
• Medical, dental, & vision coverage
• Flexible time off
• 401(k) with employer match
• WFH stipend to support your home office needs