Director of Strategic Accounts

DIRECTOR OF STRATEGIC ACCOUNTS Location: New York City (Hybrid: 2–3 days/week in office) Reports To: Head of Sales Compensation: Base: $125,000 - $175,000 | Total OTE: $175,000 - $225,000 | Equity | Benefits 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 policies, compare terms, and generate law-firm-quality insights in seconds. Our traction is undeniable: 100% pilot conversion, 20% month-over-month growth, and >150% quarter-over-quarter growth in 2025, all with minimal outbound sales or marketing. We're backed by leading venture investors including Armory Square Ventures, MTech Capital, and BrokerTech Ventures. Now we're expanding our sales team to meet demand and scale with precision. ABOUT THE ROLE Work at the forefront of insurance innovation and help shape the industry’s future with our forward-thinking partners. We're hiring our first Expansion Account Executive to be a foundational member of our go-to-market team. You'll define our customer expansion and growth playbook, own revenue retention and expansion across our portfolio, and build scalable processes as we scale from seed to Series A and beyond. You'll drive expansion revenue within existing accounts, close five and six-figure expansion deals, and ensure our customers achieve transformational outcomes that lead to renewals and advocacy. You'll work directly with our Head of Sales and founding team, with high visibility and direct impact on company strategy. This role is ideal for someone with strong P&C insurance domain expertise (broker, producer, account manager, or underwriter) eager to bring that knowledge into high-growth tech, or a proven enterprise SaaS farmer/expansion seller ready to become a category expert in insurance tech. WHAT YOU'LL DO Core Responsibilities - Own the full expansion sales cycle from opportunity identification to close with deal sizes of $25K - $250K+ expansion ACV - Actively build and manage expansion pipeline of 3-4x quota across existing accounts including brokerages, carriers, MGAs, TPAs, claims organizations, and legal teams - Drive expansion revenue through seat expansion, cross-departmental adoption, tier upgrades, and new use case identification with a goal of 120-150% net revenue retention - Manage strategic renewal negotiations with 95%+ gross retention target, identifying and mitigating churn risk proactively - Conduct consultative discovery within existing accounts to uncover new workflow challenges and build compelling expansion business cases with clear incremental ROI - Lead product demonstrations tailored to new stakeholders and departments within existing customer organizations - Navigate complex, multi-stakeholder expansion sales involving IT, Legal, Compliance, Operations, and C-suite buyers across different business units - Maintain accurate forecasting in Attio CRM with rigorous pipeline hygiene for renewals and expansion opportunities - Participate strategically in quarterly business reviews (QBRs) that demonstrate ROI, showcase wins, identify opportunities, and align on strategic priorities Strategic & Cross-Functional - Build executive relationships with C-suite and VP-level buyers in new departments and business units - Represent Qumis at tier-1 industry conferences and regional events to deepen existing relationships - Partner with Product, Marketing, and Customer Success to influence roadmap, refine messaging, create case studies, and ensure customer success drives expansion - Provide market intelligence by synthesizing competitive insights, expansion objections, and emerging use cases from existing accounts - Develop expansion sales collateral including department-specific one-pagers, incremental ROI calculators, expansion pitch decks, and use case guides - Identify and cultivate customer advocates for speaking opportunities, case studies, peer referrals, and new logo sales support - Document best practices and proven expansion sales motions for future farmer AE hires Innovation & Efficiency - Leverage AI-native tools (Clay, Apollo, ChatGPT, Perplexity) to automate account research, identify expansion triggers, and personalize outreach at scale - Test and iterate on expansion messaging, outbound sequences within accounts, and sales tactics - Develop scalable expansion processes including account planning frameworks, opportunity qualification criteria, and renewal playbooks - Stay current on AI trends, insurance industry shifts, and enterprise expansion sales methodologies WHO YOU ARE Required Qualifications - 9+ years of experience in either: - P&C insurance (broker, producer, underwriter, account manager, claims) with commercial acumen, OR - Enterprise B2B SaaS expansion sales or farmer AE role with $100K+ ACV deals - Proven track record of consistently hitting or exceeding expansion quota (top 20% performer) with >120% net revenue retention - Farmer mentality who thrives on deepening relationships, identifying expansion opportunities, and maximizing customer lifetime value - Experience selling to VP/C-level buyers in expansion scenarios and navigating complex, multi-threaded enterprise sales cycles across business units - Strong business acumen with ability to build incremental ROI models and articulate expansion value in financial terms - Excellent communication with gravitas and executive presence to conduct strategic business reviews and renewal negotiations - Consultative approach to uncovering new needs, solving problems, and positioning expansion opportunities - Entrepreneurial mindset with comfort in ambiguity and bias for action Preferred Qualifications - Deep knowledge of insurance workflows, pain points, and industry structure - Prior experience at a high-growth startup (seed to Series B) or top-tier tech company - Familiarity with AI/ML concepts and ability to explain technical capabilities to non-technical buyers - Experience with AI-native sales tools - Existing relationships within the insurance industry Success Profile You'll thrive if you: - Move fast and iterate without needing perfect information - Own outcomes, not activities—you're metrics-driven and focus on results - Embrace feedback and are committed to continuous improvement - Think like a founder and connect your work to company outcomes, no task is too small - Build trust effortlessly with customers as a strategic advisor WHY JOIN QUMIS Impact & Ownership - Foundational hire shaping the expansion sales organization, playbook, and culture from day one - High visibility working directly with the founders and senior leadership - Direct influence on product roadmap, pricing strategy, and GTM motions Category Leadership - $1.3T global insurance industry ripe for AI transformation - 100% pilot conversion, 20% MoM growth, word-of-mouth customer acquisition - Work with the most forward-thinking organizations in insurance Compensation & Growth - Top-tier pay with highly competitive base + uncapped commission - Meaningful early-stage equity with strong upside potential - Comprehensive benefits: Health, dental, vision, unlimited PTO, home office stipend Team & Culture - Small, ambitious team with backgrounds from Kin, Goldman Sachs, Archipelago, Chubb, Insureon, and American Express - Culture of experimentation, transparency, and rapid iteration - Investment in your growth through coaching, training, and industry events INTERVIEW PROCESS 1. Intro call with Head of Sales (45 min) 2. Cross-functional interviews with Customer Success and Engineering (30 min each) 3. Deeper dive with Head of Sales (45 min) 4. Final interview with CEO (45 min) 5. Reference checks and offer Timeline: 2-3 weeks. We move quickly for the right candidate. Apply