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    AI is everywhere right now. In your inbox. In your CRM. In every tool claiming to make you “more productive.” But here’s the real question:

    Is it actually helping you win deals?

    If AI isn’t improving how you execute in live opportunities then it’s just another tab open in your browser. This three-minute assessment will show you where AI is improving your execution and where it’s just a distraction.

    Check each box that’s true for you. Then total your score.

    Before deals

    • Do you use AI to prepare for specific accounts and opportunities?
    • Does AI help you identify risks, objections, or buying clues?
    • Do you use AI to tailor your message to buyers’ roles, industries, or priorities?
    • Does AI help you decide where to focus and what to ignore?
    • Do you rehearse or refine your pitches using AI feedback?

    During deals

    • Do you use AI to inform your next move in a live call?
    • Does AI surface stakeholders, engagement gaps, or deal risks based on full opportunity context?
    • Do you adjust your move based on AI insight, even when it challenges your instincts?
    • Do you use AI to develop sharper follow-ups that move deals forward?
    • When deals slow down, do you ask AI why before escalating?

    After talking to buyers

    • Do you use AI feedback to improve how you handle objections or positioning?
    • Has AI helped you spot patterns across deals, not just within a single call or opportunity?
    • In the last 30 days, have you improved a skill because AI suggested it?
    • Can you name at least one deal where AI guidance helped you move forward?
    • Are you using AI consistently across deals?

    What your score actually means

    12–15 checked boxes

    You’re using AI as part of your execution system.

    AI isn’t just helping you prepare. It’s shaping how you adjust in real time, and that consistency compounds across deals.

    Next step: Pick one high-stakes opportunity this week and go even deeper. Use AI to stress-test your strategy before the next conversation.

    8–11 checked boxes

    You’re using AI, but not consistently enough for it to shape outcomes.

    You’re on the right track, but there’s still execution lift available and the chance to improve your win rates.

    Next step: Commit to using AI in every live deal for the next 30 days, especially before meetings and when you notice a change in momentum.

    0–7 checked boxes

    AI isn’t yet part of how you execute deals.

    You have access to AI, but you haven’t built it into your daily workflow. That’s where the biggest gains are.

    Next step: Start simple. Before your next customer meeting, ask AI one question: “What’s my smartest next move in this deal?” Then act on it.

    Better execution starts now

    AI creates the most impact when it shapes how you execute, not just how you prepare.

    Two ways to start immediately:

    • Before your next meeting, ask AI one question: “What’s my smartest next move in this deal?
    • After your next call, ask: “What risk did I miss, and how should I address it?”

    Small adjustments lead to big outcomes.

    If you want to see how top performers build AI into their execution system and turn it into consistent wins, start with How Top Sellers Win in 2026.

    Brie Tobin

    Brie Tobin is an innovative and motivated sales leader with over 12 years of experience in B2B SaaS organizations. As the leader of SMB and Commercial Sales at Highspot, an industry-leading enablement platform, Brie helps sales talent strategize, build, and scale their processes to drive consistent, positive results. Known for thriving in fast-paced environments, she combines flexibility, leadership, and a wealth of best practices gained from collaborating with world-class leaders in software sales. With expertise spanning SaaS, sales enablement, funnel management, and advanced methodologies like SPIN and Corporate Visions, Brie is passionate about leveraging her experience to deliver outstanding business results. She takes pride in empowering teams and achieving measurable outcomes that drive growth and success.

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