Mid Market Account Executive | Oscar
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  • US
    • UK & EU
    • US

    Mid Market Account Executive

    • Sales Leadership, Sales Leadership
    • San Francisco, California
    • Permanent
    $100K-$125K per annum
    Benefits: OTE $250k Equity

    Mid-Market Account Executive
    šŸ“ Hybrid, San Francisco, CA (in office Tuesday through Thursday, work from home Monday and Friday)
    šŸ’° Base $100K to $120K, OTE up to $250K , equity and benefits


    About Us

    We are a VC-backed, AI Native SaaS company building a first-of-its-kind revenue platform for go-to-market teams. Unlike companies that simply add AI features, our product is AI at the core, powering warm outbound and helping sales and growth leaders connect with the right buyers at the exact moment they are ready.

    Backed by top-tier investors and already trusted by recognized customers, we have grown revenue 8x year over year and are creating a new category in go-to-market technology. This is a rare chance to join early, work with proven operators from leading startups, and have a direct hand in shaping how GTM teams win.


    The Role

    As a Mid-Market Account Executive, you will own the full sales cycle and be the face of our product for mid-market customers. This is a technical, consultative sale where you will partner with RevOps, Sales, and Marketing leaders, uncover complex needs, and show them how AI Native technology can transform their pipeline.

    This role is ideal for someone with strong closing skills, energy, and a startup mindset. You thrive in a high-growth environment, collaborate well across teams, and are motivated to exceed quota while having fun along the way.


    What You'll Do

    • Manage a healthy pipeline of inbound opportunities while occasionally generating outbound activity

    • Conduct discovery to understand business challenges and stakeholder goals

    • Deliver product presentations and demos that clearly communicate ROI and technical value

    • Navigate sales cycles of one to four months with multiple stakeholders, ensuring consistent next steps

    • Build relationships with senior decision-makers in sales, marketing, and growth functions

    • Work cross-functionally with product, marketing, and engineering to deliver customer insights and shape roadmap

    • Continuously develop your industry knowledge, technical expertise, and ability to position value effectively


    What You'll Need

    • 1.5 or more years of quota-carrying SaaS sales experience in the mid-market or enterprise segment with consistent quota achievement

    • Experience leading consultative, technical sales cycles of one to four months

    • Familiarity with RevOps, GTM workflows, or sales and marketing technology preferred

    • Excellent communication, presentation, and negotiation skills

    • Proficiency in Salesforce or similar CRM systems

    • A startup mentality, with high energy, curiosity, accountability, and collaborative spirit


    Why Join Us

    • Be part of a VC-backed AI Native startup in hypergrowth

    • Work closely with an experienced founding team and category-creating investors

    • Base salary $100K to $120K with OTE up to $250K , plus equity and full benefits

    • Hybrid schedule in San Francisco, with three days in-office for collaboration and two days remote for flexibility

    • Direct impact on customers, product direction, and the future of go-to-market

    Oscar Associates Limited (US) is acting as an Employment Agency in relation to this vacancy.

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