Head of Sales & GTM

About Qumis

Qumis is redefining insurance with generative AI. We’re building the leading vertical AI platform for insurance knowledge work—trusted by top brokers, carriers, and claims professionals to analyze complex insurance policies, compare terms, and generate law-firm-quality insights in seconds. Our platform turns generative AI into real productivity gains for an industry that runs on nuance, expertise, and dense legal language.

The traction is undeniable: we’ve converted 100% of pilot customers, are growing 20% month over month since first revenue, and have achieved 156% quarter-over-quarter growth in 2025—all without any outbound sales or marketing. We’ve caught lightning in a bottle.

Now we're hiring a Head of Sales & GTM to scale that momentum across all channels into a unified, high-performing, AI-native growth engine. You'll inherit a live pipeline with marquee pilots, warm enterprise prospects, and top-50 brokerages in evaluation, plus several high-potential partnerships with industry associations and channel partners. But this is ultimately a builder's role: you'll architect the execution of our go-to-market strategy—from onboarding funnels to six-figure enterprise deals—and lay the foundation for our path to $10M+ ARR and beyond.

We’re not looking for someone who needs SDR handoffs or enablement playbooks. We’re looking for a hands-on sales leader who thrives in ambiguity, creates leverage from scratch, and wants a career-defining role building a next-generation go-to-market function at a breakout generative AI company.

About the Role

Qumis is hiring a founding Head of Sales & GTM to lead our path from founder-led sales to a scalable, repeatable revenue machine.

This is a builder’s role—not a maintainer’s. You’ll own and lead the full sales motion from day one: driving enterprise deals, defining our go-to-market strategy, and helping us scale from early momentum to $10M+ in ARR. You’ll work directly with the CEO and help define how Qumis sells, how we grow, and what great looks like.

In the first 6–12 months, you’ll operate as an IC leader: prospecting, selling, running enterprise pilots, and closing six-figure deals with some of the largest and most respected firms in insurance. At the same time, you’ll lay the foundation for a world-class GTM function—from outbound systems and ABM campaigns to PLG conversion paths and team structure. You’ll then hire and scale the GTM team you’ve designed.

You’ll collaborate tightly with product, marketing, and customer experience to drive the next phase of growth across sales-led and product-led channels.

What You’ll Do

Enterprise Sales & Pipeline Development

• Own the full enterprise sales cycle—from outbound prospecting through discovery, pilot, proposal, negotiation, and close

• Build a high-quality, targeted pipeline across brokerages, carriers, MGAs, TPAs, and legal service providers

• Execute and close six-figure+ deals with multi-stakeholder buying committees (claims, legal, operations, tech, exec)

• Run fast-moving pilots with urgency and clear paths to paid conversion

• Stand up repeatable outbound and ABM programs to reach top-100 accounts

Go-to-Market Strategy & Execution

• Define Qumis’s GTM strategy—customer segmentation, pricing, packaging, messaging, and channel mix

• Partner with the CEO to craft strategic narratives and define where and how we win

• Refine and operationalize the sales process, from CRM workflows to sales enablement content

• Establish clear qualification, handoff, and upsell processes between inbound, product-led, and outbound motions

Product-Led Sales & Expansion

• Build the bridge between product-led signups and enterprise conversion

• Design usage triggers, upgrade flows, and expansion playbooks that move self-serve users into high-value deals

• Collaborate with product and customer experience on onboarding, activation, and retention improvements

• Use product signals to prioritize accounts and inform outbound GTM

Foundational Infrastructure

• Build the sales and GTM foundation: CRM, forecasting, dashboards, attribution, and workflows

• Set up systems and tooling for efficient outbound, pipeline tracking, and deal management

• Lead win/loss analysis and continuously improve messaging and playbooks based on customer feedback

• Own sales forecasting and pipeline health reporting for executive stakeholders

Hiring & Leadership

• Be the founding go-to-market leader—both closing deals and building the system

• Hire and coach future AEs, BDRs, and GTM teammates as the team scales

• Act as a strategic advisor to the CEO and a thought partner across growth and product decisions

• Represent Qumis with professionalism and credibility in customer and industry conversations

Ideal Candidate Profile

• 7–12+ years of experience in high-growth B2B SaaS, with a focus on enterprise sales and GTM ownership

• Track record of closing complex six-figure+ enterprise deals from outbound to close

• Experience building GTM foundations in early-stage startups or zero-to-one environments

• Deep understanding of sales process design, account-based selling, and pipeline development

• Exposure to product-led growth motions and an ability to convert product usage into enterprise expansion

• Strategic thinker with strong execution chops—can both zoom out and roll up sleeves

• Consultative, persuasive, and comfortable navigating complex stakeholder environments

• Entrepreneurial mindset—you want to build, own, and scale something lasting

• Insurance industry experience or network is a strong plus, but not required

• High integrity, high urgency, and high standards

What You’re Walking Into

• A warm, qualified pipeline across top-100 brokerages, carriers, and claims organizations

• Multiple live enterprise pilots with clear ROI and engagement

• Strong product-market fit signals and repeatable early wins

• Early product usage and self-serve motion primed for expansion

• A founder-led sales engine you’ll build on, not replace

• Deep customer trust and references, industry interest, and clear economic value delivered

Why Join Qumis

• Backed by top-tier venture capital funds including Armory Square Ventures, MTech Capital, Grand Ventures, and Alumni Ventures, and strategic angels in AI and insurance including the founder and CEO of Chicago insurtech unicorn Kin Insurance

• Used and loved by leading brokerages and claims teams to transform how work gets done including multiple top 15 brokerages with tremendous expansion potential

• Shape the future of how generative AI transforms one of the world's most complex, critical industries

• High-ownership role on a high-standards founding team with grit, urgency, and big ambition

• Build a generational company—the kind of opportunity that only comes once in a career

We've Got You Covered

We offer a comprehensive benefits package so you can choose what’s best for you and your family. Our benefits include:

• Medical, dental, and vision insurance (Aetna + Guardian) with 100% of premiums covered for employees on select plans and up to 90% coverage for dependents

• Life Insurance (company-paid), plus supplemental options, short- and long-term disability insurance, pre-tax FSA and HSA options, and pre-tax commuter benefits

• Unlimited PTO & $1,000 home office setup stipend

• Hybrid work environment: 1–2 days/week in our Chicago office

• Professional development support and growth opportunities