Head of Sales

About Us Cachet is building the insurance infrastructure to help Europe's platform economy thrive. Our technology and services are enabling platforms to control risk and prevent loss at scale. Role Summary Lead Cachet's full sales function: owning both new business and key account management, carrying a personal quota on senior deals, and building the commercial playbook for new market expansion. The Role We're hiring a Head of Sales to own Cachet's full sales function: both new business and key account management. You'll lead the Account Executive and Key Account Manager teams, set the bar for pipeline quality, deal execution, and customer growth, and personally close the deals that require senior commercial weight. This is a player-coach role: you'll spend part of your time coaching your teams, running pipeline and account reviews, and building a high-performance sales culture, and part of your time in the room with enterprise prospects and strategic accounts, driving complex cycles from discovery to close. You'll report to the CRO and work closely with Revenue Operations on pipeline discipline and forecasting accuracy. What You'll Do AE Team Leadership & Coaching Lead and develop the Account Executive and Key Account Manager teams: setting individual targets, coaching on deals and account plans, reviewing pipeline quality and account health, and building a high-performance sales culture. Run weekly pipeline and account reviews: ensuring AEs have a healthy, well-qualified new business pipeline and KAMs are progressing expansion and renewal opportunities with clear next actions. Deliver structured coaching and deal support across both teams: joining calls, reviewing proposals, providing objection-handling guidance, and helping the team close and grow more effectively. Onboard new sales hires: ensuring they understand Cachet's sales process, product, ICP, and competitive positioning, and that they reach productivity quickly. Act as the escalation point for complex deals, pricing decisions, or key account issues that require senior commercial judgement. Personal New Business Sales Carry a personal new business quota: managing a pipeline of senior prospects and target accounts that require Head of Sales-level engagement. Lead commercial conversations with enterprise and strategic prospects: running the full sales cycle from discovery through proposal to close. Build and maintain relationships with senior decision-makers at target accounts: acting as Cachet's senior commercial face in new business contexts. Represent Cachet at industry events, trade shows, and networking opportunities: generating pipeline through personal commercial presence. Market Expansion & Branch Leadership Work with the CRO and Chief of Staff on the go-to-market approach for new geographies: translating market-entry strategy into commercial execution. As branch operations grow, build and lead local commercial teams: recruiting, onboarding, and managing branch-level sales staff. Ensure the commercial playbook, processes, and culture developed at HQ translate effectively to branch operations. Sales Process & Standards Champion consistent application of the sales methodology across both the AE and KAM teams, ensuring qualification standards, CRM hygiene, pipeline stage discipline, and account management rigour are maintained. Work with Revenue Operations to ensure pipeline and account data is accurate, up to date, and usable for forecasting, covering both new business and expansion revenue. Identify gaps in the sales process, tooling, or enablement and escalate with proposed solutions. Feed first-hand prospect and customer intelligence into strategic planning: helping shape Cachet's commercial positioning and competitive response. What We're Looking For 5+ years of B2B sales experience, with at least 2 years leading or managing a sales team across both new business and account management. Proven track record of personally closing complex, multi-stakeholder deals, not just managing a team from the sidelines. Experience building or scaling a sales function: you've set up pipeline processes, account management frameworks, coached salespeople, and driven a team to hit targets. Strong commercial judgement across the full customer lifecycle, from winning new logos to growing and retaining existing accounts. Comfortable operating in a fast-moving, founder-led environment where you'll need to build as much as you execute. Excellent English communication skills, written and verbal. Nice to Have Experience in insurtech, fintech, or platform/marketplace businesses. Background in selling to enterprise or mid-market customers in regulated industries. Experience opening new markets or geographies, whether through branch setups, partnerships, or direct market entry. Familiarity with MEDDIC, SPIN, or similar structured sales methodologies. Work Setup This is a hybrid role. Our HQ is in Tallinn, where the team works together regularly each week. Remote work is welcome, but we expect monthly in-person collaboration in Tallinn to stay connected and aligned. English is our working language, and EU work authorisation is required. Recruitment Process Overview 1. Intro with the HR (30 min) 2. Interview with the CRO (1 h) 3. Case task (approx 2 h to prepare) 4. Case presentation (20 min) and interview with the CEO and CRO (40 min) This role is hired on an ongoing basis and applications are reviewed continuously.