Chief of Staff to the Head of Sales

Assured is on a mission to modernize insurance. Claims processing (i.e. should we pay this claim?), while often overlooked, is the foundation of the entire industry. It’s currently highly manual, involving phone calls, faxes, and gut instinct, costing tens of billions of dollars a year. We can do better. At Assured, we provide large insurers with the software solutions they need to win in a modern, technology-driven world. From self-service claim-filing software to backend fraud detection, we’re the engine that powers claims processing for some of the largest insurers in the world. The challenges we face are deep and diverse, from creating digital experiences that provide comfort and clarity to claimants at their most stressed and vulnerable to orchestrating large-scale ML-driven decision-making on billions of dollars of claims payments, life at Assured is dynamic, collaborative, and rewarding. We are looking for a Chief of Staff to the Head of Sales to serve as the right hand to our sales leadership and act as a force multiplier across the go-to-market organization. This is a rare role that sits at the intersection of sales strategy and execution, putting you shoulder to shoulder with the Head of Sales on the decisions, deals, and operating rhythms that drive revenue. Assured’s sales motion increasingly includes a Forward Deployed Team (FDT) model. Our teams work alongside carrier executives and operators to identify high-value claims problems, understand the carrier’s data and workflows, co-create solutions, and move from discovery to measurable production value. You will not lead or own this motion. You will support the Head of Sales and accountable sales leaders by improving meeting readiness, internal alignment, resource coordination, visibility into commitments and risks, and follow-through. You will move between the strategic and the tactical without missing a beat: one hour building the ELT ready deal strategy, the next unblocking a stalled enterprise deal or standing up a new sales operations process. This role is for someone who thrives in ambiguity, brings structure to chaos, and takes pride in making the people around them, starting with the Head of Sales, dramatically more effective. If you want direct exposure to how a high-growth company wins in the market, and the chance to shape the sales engine behind that growth, this is your seat. What You'll Do You will own a broad, rotating portfolio spanning sales strategy, operations, and execution. In practice, that means: 🤝 Serve as the right hand to the Head of Sales - Act as a trusted thought partner and proxy: manage the sales leader's strategic agenda, prepare them for high-stakes internal and customer meetings, and make sure priorities translate into action and accountability. 📅 Own the sales operating cadence - Design and run the rhythm of the business, including pipeline reviews, forecast calls, QBRs, staff meetings, and sales off-sites, ensuring each is well-prepared, decision-oriented, and followed through. 📊 Drive pipeline visibility and forecasting - Build and maintain the reporting, dashboards, and analysis that give leadership a clear, accurate view of pipeline health, forecast accuracy, and team performance. 🎯 Own sales enablement - Design and build the decks, one-pagers, and narratives the team uses in critical customer meetings, and make sure reps have what they need to win. 🔗 Lead cross-functional coordination - Act as the connective tissue between Sales and Marketing, Customer Engineering, Product, and Finance, driving alignment on handoffs, launches, and shared GTM priorities. 🧩 Structure complex problems - Apply rigorous analytical frameworks to ambiguous questions such as segmentation, territory strategy, pricing inputs, and win/loss analysis, turning data and qualitative insight into actionable recommendations. 🌟 Support key hiring and onboarding - Partner on recruiting, interviewing, and onboarding across the sales organization to help attract and ramp top talent quickly. 📝 Prepare executive-level materials - Build the strategic memos and internal communications that represent the sales function to the executive leadership team. What You'll Bring 💼 5-7 years of experience, including 2-4 years at a top-tier management consulting firm (Bain, McKinsey, BCG or equivalent) or in a sales strategy, revenue operations, or chief-of-staff role at a high-growth company. 💬 Exceptional communication, both in writing and in the room, with the ability to drive complexity into clarity for any audience, including customers and executives. 📈 Strong analytical horsepower, and comfort building models, pipeline analyses, and strategic frameworks from scratch. 🚀 An execution-oriented mindset: you follow through, hold timelines, and get things done without being managed. 💪 A high degree of ownership and a low ego: you are comfortable doing the thinking and the doing, and no task is too big or too small. 🤝 Experience managing or influencing cross-functional teams without formal authority. 🛠️ Familiarity with modern sales tooling (CRM, sales engagement, and BI or reporting platforms) is a plus. Benefits: 🤑 Competitive Compensation: Competitive salary and equity packages for all employees 🏥 Healthcare Plan: Platinum medical, dental, and vision 🛡️ Free life insurance: Including long-term disability & short-term disability 🏄 Unlimited PTO: Uncapped vacation days & paid holidays 👶 Family Leave: Maternity & paternity 📈 401(k) Contribution: Assured contributes 3% of your income, even if you don't contribute 🏠 WFH Benefits: Lunch on us 2x/week, monthly phone stipend & other home office perks 👪 Health FSAs & HSAs: Pre-tax accounts for out-of-pocket medical expenses 🤝 Team events & Offsites: We're remote, but we regularly get together **We have been made aware of individuals falsely posing as recruiters from Assured Insurance Technologies Inc. Please note that we only contact candidates from official @ assured.claims email addresses and all interviews are conducted through verified company channels. If you are unsure whether a message is legitimate, please contact us directly at before sharing any personal information ** Our Commitment: We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, sex, gender, gender expression, sexual orientation, age, marital status, veteran status, or disability status. We will ensure that individuals with disabilities are provided reasonable accommodation to participate in the job application or interview process, perform essential job functions, and receive other benefits and privileges of employment. Please contact us to request accommodation.