(Founding) Insurance Account Executive

🧡 Coverflex Coverflex started with a simple observation: work changed, but compensation didn’t. A few founders looked at how people were being paid across Europe — rigid salary structures, fragmented benefits, systems that were complex for HR and often meaningless for employees — and realized the model simply hadn’t kept up with modern work. So we decided to rebuild it. What began in Portugal as a small team trying to fix a broken compensation system quickly grew into one of the most ambitious compensation platforms in Southern Europe. Today, thousands of companies use Coverflex to manage benefits, meal allowance, insurance, and flexible compensation through a single platform. But what makes Coverflex special isn’t just the product — it’s how we build. We’re a team of people who like solving hard problems, moving fast, and taking real ownership. We care about clarity, autonomy, and impact. Titles matter less than outcomes, and good ideas can come from anywhere. Now we’re entering our next chapter. After building strong traction in Portugal, Spain, and Italy, we’re expanding into Germany — one of Europe’s most sophisticated and complex compensation markets. Launching a new country at Coverflex isn’t about “copy-pasting” what already exists. It’s about building again — understanding the market, challenging old assumptions, and creating something that truly works for local companies and employees. If you join at this stage, you won’t just be joining a company. You’ll be helping build the next chapter of it. ⚙️ TL;DR (The Essentials) Role: (Founding) Insurance Account Executive Seniority Level: Intermediate Type: Individual Contributor Languages: English (main) / German (C2). Portuguese / Spanish / Italian are a plus Main Tools: HubSpot, LinkedIn Sales Navigator, Notion, Slack Regulatory requirement: §34.d Gewerbeordnung (GewO) Location: Remote (Germany) Compensation: • OTE: €85.000 - €95.000 (70/30) • Equity: Yes – Stock Options under our Equity Incentive Plan • Benefits: you can check them below (at the end of the page) • Contract Type: Permanent 💥 Your Impact As the Founding Insurance Account Executive for Germany, you will help build Coverflex’s insurance business in Germany from the ground up — with a primary focus on betriebliche Altersvorsorge (bAV) and related corporate pension solutions. This is a full-cycle B2B sales role with a genuine B2B2C dimension: you'll prospect and close employer deals, then support employee adoption through town halls, advisory sessions, and enrollment events. You won't just win accounts — you'll make them successful. Beyond individual deals, you'll contribute to our go-to-market strategy, feed market insights back into product and partnerships, and help establish Coverflex as a credible, trusted name in the German employee benefits space. What You'll Own • Full sales cycle from outbound prospecting through to close, primarily targeting HR, People, Finance, and C-level stakeholders at mid-size and enterprise employers • Building and managing a bAV expansion pipeline within existing Coverflex accounts • Running employee-facing events — town halls, individual and group advisory sessions, and enrollment support — as an integral part of the sales motion • CRM discipline: activity tracking, pipeline hygiene, accurate forecasting in HubSpot • Contributing to playbooks, process documentation, and feedback loops that shape how we sell insurance in Germany long-term You’ll know you’re successful when, after 90 days, you’ve… • Built a clear expansion pipeline across your portfolio and started converting opportunities into revenue • Proven you can balance volume with quality conversations and consultative selling • Earned the trust of key customer stakeholders (HR, Finance, C-level) and employees • Developed strong CRM discipline (activity tracking, notes, next steps) • Started forecasting with consistency and accuracy • Started creating repeatable structures and processes to sell bAV into existing customers How We’ll Measure Success • Main KPI 1: New ARR generated (closed-won deals) • Main KPI 2: Number of expansion opportunities identified, qualified, and closed • Main KPI 3: Portfolio engagement metrics (meetings booked, calls made, conversion rates) ⚡ Reality Check – What Makes This Role Hard Let’s be real, this is not a “relationship manager” role where things just flow. Here’s what makes it challenging: • You’ll help build structure where it doesn’t fully exist yet, contributing to playbooks, processes, and feedback loops that will shape how our GTM motion works in Germany • You’ll manage a high volume of accounts and still need to maintain quality, value-driven conversations. You’ll have to manage both employer and employee relationships • Rejection is part of the job. Not every lead converts, and you need the resilience to keep going, adapt, and improve — not wear down • You’ll navigate multiple decision-makers, especially HR + Finance who may have different priorities • You’ll need to be consistent with high volume (calls/emails every day) while keeping energy and focus high • You’ll be expected to hit targets in a consultative environment where trust-building and timing matter 👤 You Must-haves (evidence, not years) • Proven track record working with Corporate Pensions • Insurance Mediation/Distribution License — §34.d Gewerbeordnung (GewO) • Proven B2B Sales or Customer Success experience with commercial responsibility • Comfortable owning expansion conversations across stakeholders (HR, Finance, C-level) • Highly organized and disciplined managing portfolio activity and follow-ups • Confident hitting targets through structured execution and pipeline discipline • Strong CRM mastery (e.g., HubSpot/Salesforce) • Sachkundenachweis (proof of professional competence): You must demonstrate professional qualifications. This is typically done by successfully passing the IHK-Sachkundeprüfung für Versicherungsvermittler (Chamber of Commerce and Industry examination of expertise for insurance intermediaries), or through a recognized vocational training, e.g. as a Versicherungskaufmann (qualified insurance clerk) • Persönliche Zuverlässigkeit (personal reliability/trustworthiness): A clean Führungszeugnis (certificate of good conduct) and a statement from the Schuldnerverzeichnis (debtor register) or the central Vollstreckungsportal (enforcement portal) Nice-to-have • Experience in Disability insurance (bBU), Corporate health insurance (bKV), and Long-term care insurance (bPV) • Familiarity with the HR or benefits space • You've worked in a startup or fast-paced scale up — you know what "figure it out" mode looks like • Public speaking, training, or webinar hosting experience 🧬 Your DNA • Proactive: you don’t wait for accounts to ask, you create opportunities • Growth-oriented: feedback fuels you, it doesn’t trigger you • Organised & data-driven: your pipeline isn’t “in your head”, it’s in the CRM • Resilient: you can hear “not now” 10 times and still show up sharp on call 11 • Executive-ready communicator: you’re clear, confident, and credible with senior stakeholders • Collaborative: you win as a team, not as a solo hero You’ll probably find this frustrating if… • You have a low ownership mindset or need constant direction • You’re uncomfortable with targets, outreach volume, or quota pressure • You lack structure and struggle to manage multiple accounts at once • You prefer working alone and avoid cross-functional collaboration 👥 Manager & Team Meet Your Manager Hiring Manager: Mateusz Witjes - Head of Sales Location: Germany LinkedIn Profile: https://www.linkedin.com/in/mateusz-witjes-06aa8a156/ Profile Snapshot: • Energy: Resilient under pressure, competitive, results-oriented, hands-on • Communication: Confident, clear, motivating, comfortable with tough, transparent conversations • Feedback Style: Straightforward, constructive, timely, perf