Head of Sales

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    "jobOpeningName": "Head of Sales",
    "departmentLabel": "Sales",
    "employmentStatusLabel": "Full-Time"
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    "location": {
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      "state": "Harjumaa",
      "postalCode": "10134",
      "addressCountry": "Estonia"
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    "datePosted": "2026-05-31",
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    "description": "<p><span style=\"font-family: Arial, sans-serif; font-size: 10pt; font-weight: bold\">About Us</span></p>\n<p><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">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.<br><br></span></p>\n<p><span style=\"font-family: Arial, sans-serif; font-size: 10pt; font-weight: bold\">Role Summary</span></p>\n<p><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">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.<br><br></span></p>\n<p><span style=\"font-family: Arial, sans-serif; font-size: 10pt; font-weight: bold\">The Role</span></p>\n<p><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">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.</span></p>\n<p><span style=\"font-family: Arial, sans-serif; font-size: 10pt\"><br></span><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">You'll report to the CRO and work closely with Revenue Operations on pipeline discipline and forecasting accuracy.<br><br></span></p>\n<p><span style=\"font-family: Arial, sans-serif; font-size: 10pt; font-weight: bold\">What You'll Do</span></p>\n<p><span style=\"font-family: Arial, sans-serif; font-size: 10pt; font-weight: bold\">AE Team Leadership &amp; Coaching</span></p>\n<ul>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">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.</span></li>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">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.</span></li>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">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.</span></li>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">Onboard new sales hires: ensuring they understand Cachet's sales process, product, ICP, and competitive positioning, and that they reach productivity quickly.</span></li>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">Act as the escalation point for complex deals, pricing decisions, or key account issues that require senior commercial judgement.</span></li>\n</ul>\n<p><span style=\"font-family: Arial, sans-serif; font-size: 10pt; font-weight: bold\">Personal New Business Sales</span></p>\n<ul>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">Carry a personal new business quota: managing a pipeline of senior prospects and target accounts that require Head of Sales-level engagement.</span></li>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">Lead commercial conversations with enterprise and strategic prospects: running the full sales cycle from discovery through proposal to close.</span></li>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">Build and maintain relationships with senior decision-makers at target accounts: acting as Cachet's senior commercial face in new business contexts.</span></li>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">Represent Cachet at industry events, trade shows, and networking opportunities: generating pipeline through personal commercial presence.</span><br></li>\n</ul>\n<p><span style=\"font-family: Arial, sans-serif; font-size: 10pt; font-weight: bold\">Market Expansion &amp; Branch Leadership</span></p>\n<ul>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">Work with the CRO and Chief of Staff on the go-to-market approach for new geographies: translating market-entry strategy into commercial execution.</span></li>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">As branch operations grow, build and lead local commercial teams: recruiting, onboarding, and managing branch-level sales staff.</span></li>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">Ensure the commercial playbook, processes, and culture developed at HQ translate effectively to branch operations.</span></li>\n</ul>\n<p><span style=\"font-family: Arial, sans-serif; font-size: 10pt; font-weight: bold\">Sales Process &amp; Standards</span></p>\n<ul>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">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.</span></li>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">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.</span></li>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">Identify gaps in the sales process, tooling, or enablement and escalate with proposed solutions.</span></li>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">Feed first-hand prospect and customer intelligence into strategic planning: helping shape Cachet's commercial positioning and competitive response.</span><span style=\"font-family: Arial, sans-serif; font-size: 10pt\"><br><br></span></li>\n</ul>\n<p><span style=\"font-family: Arial, sans-serif; font-size: 10pt; font-weight: bold\">What We're Looking For</span></p>\n<ul>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">5+ years of B2B sales experience, with at least 2 years leading or managing a sales team across both new business and account management.</span></li>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">Proven track record of personally closing complex, multi-stakeholder deals, not just managing a team from the sidelines.</span></li>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">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.</span></li>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">Strong commercial judgement across the full customer lifecycle, from winning new logos to growing and retaining existing accounts.</span></li>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">Comfortable operating in a fast-moving, founder-led environment where you'll need to build as much as you execute.</span></li>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">Excellent English communication skills, written and verbal.</span></li>\n</ul>\n<p><span style=\"font-family: Arial, sans-serif; font-size: 10pt; font-weight: bold\">Nice to Have</span></p>\n<ul>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">Experience in insurtech, fintech, or platform/marketplace businesses.</span></li>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">Background in selling to enterprise or mid-market customers in regulated industries.</span></li>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">Experience opening new markets or geographies, whether through branch setups, partnerships, or direct market entry.</span></li>\n<li><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">Familiarity with MEDDIC, SPIN, or similar structured sales methodologies.<br><br></span></li>\n</ul>\n<p><span style=\"font-family: Arial, sans-serif; font-size: 10pt; font-weight: bold\">Work Setup</span></p>\n<p><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">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.<br><br></span></p>\n<p><span style=\"font-family: Arial, sans-serif; font-size: 10pt; font-weight: bold\">Recruitment Process Overview</span></p>\n<p><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">1. Intro with the HR (30 min)</span></p>\n<p><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">2. Interview with the CRO (1 h)</span></p>\n<p><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">3. Case task (approx 2 h to prepare)</span></p>\n<p><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">4. Case presentation (20 min) and interview with the CEO and CRO (40 min)<br><br></span></p>\n<p><span style=\"font-family: Arial, sans-serif; font-size: 10pt\">This role is hired on an ongoing basis and applications are reviewed continuously.</span></p>",
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    "minimumExperience": "Senior Manager/Supervisor",
    "jobOpeningShareUrl": "https://cachet.bamboohr.com/careers/58",
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