Frontline Strategist

About WorkWhile

WorkWhile is on a mission to help workers earn a better living and live better lives. More than 80 million Americans work hourly jobs, often with unpredictable schedules that pay close to minimum wage and offer limited benefits, leading to financial instability.

WorkWhile is revolutionizing frontline work by creating a more flexible and efficient labor market. Powered by AI, the WorkWhile platform helps businesses quickly access high-quality talent. Workers benefit from same-day pay, free telehealth services, upskilling, and the ability to choose shifts that match their skills and schedules.

We have the audacious goal to align incentives and solve inefficiencies in the labor market, disrupting the $650 billion staffing and recruiting market. Backed by Khosla Ventures and recognized by the Inc. 5000 for 10x growth, WorkWhile is reshaping the future of work.

About the role

We're building a category-defining Frontline Deployed Engineering (FDE) pod: a world class team focused on going deep with key enterprise customers, understanding their operational reality, and building solutions that make WorkWhile genuinely work for them. Our ultimate goal is to compress time to PMF-at-scale for key accounts and compound learnings across the portfolio.

As our first Frontline Strategist (Product Manager), you'll be the connective tissue of this pod. You'll work directly alongside our Frontline Engineers and customers to define what gets built, why, and in what order, translating messy field problems into clear product direction. You'll report to our Head of Product and work closely with our CEO on the vision for this motion.

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

WorkWhile has a diverse, mission-driven, and supportive culture—we look for people who want to take ownership, are energized by ambiguity, and strive to make a lasting impact. If this resonates with you, we’d love to chat!

WorkWhile is an Equal Opportunity Employer. Women, minorities, individuals with disabilities and protected veterans are encouraged to apply.