We are seeking a Head of Commercial Strategy to work with the General Manager to establish Bloom, Sword's AI-powered women's health solution, as the category leader across health plans, self-insured employers, brokers, consultants, and platform partners. This is not a quota-carrying sales role. This is a high-impact individual contributor leadership role. You will not manage a team, but you will be expected to drive outsized strategic impact through personal expertise, relationships, and influence across the organization. The role is focused on market positioning, competitive differentiation, pipeline generation, and commercial intelligence that ensures Bloom wins against every incumbent in the women's health space.

Starting with pelvic health and now expanding into menopause, fertility, pregnancy, and postpartum care, Bloom is powered by the same AI Care model driving Sword's platform: a continuous interaction between the member, an AI health specialist (Phoenix), and a human clinician. 

The Head of Commercial Strategy will be the external face of Bloom's commercial narrative and the internal voice of the market, shaping how the product is positioned, how the pipeline is built, and how the product itself evolves to win.

This role is critical to our success. You will determine how health plans, brokers, consultants, and employers perceive Bloom relative to every alternative on the market. You will ensure our sales teams walk into every room with an unfair advantage — the positioning, the proof points, the relationships, and the market intelligence to win at north of 75-80% against established women's health solutions like Maven Clinic, Midi Health, Progyny, Carrot Fertility, amongst others. You will also close the loop from market to product, ensuring what we build reflects what the market needs to see us as the unambiguous category leader.

What you'll be doing:

Category Leadership & Market Positioning

Define and own the category narrative for AI-powered women's health across the full life stage continuum, positioning Bloom as the definitive next-generation platform that makes fragmented, condition-specific point solutions obsolete.

Build and maintain a comprehensive competitive intelligence operation against existing Women’s Health solutions in the market — understanding their positioning, pricing, clinical evidence, and client traction.

Develop differentiated positioning by buyer persona: health plan medical directors, employer benefits leaders, broker/consultant advisors, and platform/channel partners.

Create and evangelize the "why Bloom wins" narrative backed by clinical evidence, AI differentiation, outcomes-based pricing, and total cost of care impact.

Author thought leadership content — white papers, conference presentations, webinars, op-eds, and industry panel appearances — that establishes Bloom and Sword as the intellectual leader in women's health AI care.

Pipeline Generation & Commercial Enablement

Generate qualified pipeline for the sales team through relationship-driven business development, strategic partnerships, conference presence, and thought leadership — not through direct deal closing.

Build and leverage a deep personal network across health plans, brokers, benefits consultants, employer coalitions, and industry associations to open doors and create warm introductions at scale.

Create world-class sales enablement materials — competitive battle cards, objection handling guides, RFP response frameworks, case studies, ROI models, and pitch narratives — that give our sales teams an unfair advantage in every conversation.

Partner with the broader sales organization to support upstream deal strategy, competitive positioning in active opportunities, and win/loss analysis to continuously improve our approach.

Support strategic client conversations and finalist presentations where deep market expertise and credibility are needed to close — without carrying a personal quota.

Client Transition & Cross-Sell Strategy

Develop and execute the strategic playbook for transitioning existing Sword clients to Bloom's women's health solution, ensuring a compelling narrative from pelvic health to comprehensive women's health.

Identify and prioritize cross-sell and upsell opportunities within the existing client base, working with account management and sales to drive net new bookings from existing relationships.

Create compelling business cases and ROI narratives that make the expansion an obvious decision for current clients — particularly around menopause care.

Product Strategy Influence

Serve as the voice of the market inside the Bloom product team, translating buyer needs, competitive gaps, and market trends into actionable product strategy inputs.

Inform the product roadmap by surfacing what health plans, employers, and brokers are asking for, what competitors are building, and where the women's health market is heading.

Partner with the Head of Product to ensure clinical evidence strategy, feature prioritization, and product packaging align with what wins in the market.

Collaborate with the clinical and data teams to build the evidence base (studies, outcomes reports, case studies) that reinforces category leadership.

Industry Presence & Relationships

Represent Bloom at major industry conferences as a visible, credible voice.

Cultivate relationships with key industry analysts, consultants, and influencers who shape buyer perception and vendor shortlists.

Build and maintain a personal brand as a thought leader in women's health innovation and AI-powered healthcare delivery.

Develop strategic partnerships with industry bodies, research institutions, and clinical organizations that elevate Bloom's credibility and reach.

What you need to have:

10-15 years of experience in healthcare strategy, commercial strategy, product marketing, or business development within digital health, health plans, benefits consulting, or healthcare technology.

Deep, established relationships across the health plan, broker/consultant, and employer benefits ecosystem — a genuine network that opens doors, not just a LinkedIn network.

Proven track record of positioning a product or solution as a category leader in a competitive healthcare market, with measurable impact on pipeline generation and win rates.

Experience going head-to-head with established digital health solutions and winning — you understand the women's health competitive landscape and know how these buying decisions get made.

Strong understanding of health plan and employer purchasing processes, including RFP cycles, broker/consultant influence, medical director evaluation criteria, and benefits committee decision-making.

Exceptional storytelling and communication skills — you can command a room at HLTH, write a compelling white paper, and build a battle card that a sales rep actually uses.

Strategic thinker who can translate market intelligence into product strategy recommendations and commercial positioning.

Comfort operating at the intersection of product, marketing, and sales without owning any single function — you are the connective tissue.

Genuine empathy and passion for women's health — a mission that requires someone who understands not just the commercial landscape, but the lived experience of the population we serve.

Self-starter who thrives in ambiguity and can build a function from scratch in a fast-moving environment. This is an IC role — you will drive impact through personal expertise and influence, not through managing a team.

What we would love to see:

Direct experience in women's health, pelvic health, menopause, fertility space — either as a vendor, payer, consultant, or buyer.

Track record as a recognized thought leader or speaker in women's health, digital health, or healthcare innovation.

Experience at high-growth health tech companies where you've helped establish or disrupt a product category.

Understanding of AI-native healthcare products and the ability to articulate technical differentiation to non-technical buyers.

Experience with outcomes-based or value-based pricing models and how to position them as a competitive advantage.

Background in management consulting, health plan strategy, or benefits consulting before moving to an operating role.

Understanding of how women's health intersects with benefits equity, DE&I initiatives, and total workforce productivity — and how to use this as a commercial lever.

Proficiency leveraging AI tools to accelerate research, content creation, and competitive analysis.

How success is measured in this role:

This is a non-quota IC role, but it is not a soft role. You will be held to clear, measurable outcomes:

Pipeline generated

Competitive win rate

Net new bookings influenced

Client expansion rate to life stages

Sales enablement adoption