Why AI Coaching Is the Key To Hitting Sales Quota in 2025

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    Nearly three-quarters of sales reps expect to miss their quotas. AI coaching is changing that.

    The vast majority of sales reps are failing.

    Over the past two years, the state of sales performance has been dire. In 2024, 67% of sellers surveyed told Salesforce they expected to miss quota — and 84% reported missing quota in 2023.

    Why are so many sales reps falling short? B2B buyers now have extremely high expectations from the sales process, and sellers are fighting to deliver personalised experiences in a fiercely competitive market. The job isn’t easy.

    But for sales reps to overcome the odds and meet their goals, they need coaching. Every sales rep needs to be a product expert, a persuasive communicator, and a clever negotiator. You have to give sales reps personalised attention and guidance to help them develop those skills, and you have to deliver that feedback as quickly as possible. Timely coaching can address small issues before they turn into deal killers, and it can help instill fundamental skills that will help your sales reps in every deal going forward.

    But here’s the problem: no sales manager has the bandwidth to deliver timely, personalised feedback to every member of their team. Your team of a dozen sales reps could each be taking 10-15 meetings per week, leaving you with hundreds of call recordings to review to give useful guidance.

    This challenge of scale previously felt insurmountable. However, new advances in AI are finally tipping the scales in favour of sales managers.

    AI helps sales managers scale up coaching

    Coaching is built on a basic feedback loop. The inputs are the actions of the person being coached — whether that’s a baseball swing, a figure skating jump, or a sales conversation. The coach will observe that action, make an assessment, and then issue an output — actionable guidance that helps the person improve on their next attempt. Ideally, your guidance will help the person being coached to improve their technique for the long-term, making adjustments that will pay off in every attempt going forward. There will always be something to improve or refine — the job of a coach is never finished.

    For sales coaching, AI can help to automate both the inputs and the outputs of that feedback loop. The biggest barrier to delivering personalised feedback at scale is the sheer volume of recordings you have to sift through as a sales manager. AI tools backed by large language models can analyse meeting recordings in a matter of minutes, distilling each session down to a few key takeaways and assessing critical sales skills. Those bullet points will allow you to recognise the issues at hand without having to sit through the entire call.

    When it comes time to deliver feedback, you can also use AI to get a running start. GenAI can help you draft written feedback for each member of your sales team, tailored to their specific needs based on examples of what good looks like and the takeaways from their meeting recordings.

    The time saved by AI gives sales managers the chance to finally provide meaningful coaching to every member of their sales team. However, you don’t have to cede the territory entirely to AI. You can take a “human in the loop” approach to AI sales coaching by reviewing and adjusting AI-generated feedback to ensure it’s clear, useful, and empathetic. You should also take the time to occasionally validate the takeaways that AI is generating from each sales meeting — ensuring your AI tools are aligned with how your sales leaders would assess skill performance.

    Over time, your AI assistants will only get better. As they gather more data on your products, your team members, and your company’s goals, AI coaching tools will deliver more precise and actionable feedback. Investing in AI coaching helps you create a rising tide that lifts your entire sales team.

    No sales rep is an island

    Your sales team needs attention, investment, and support to grow and succeed. There’s no substitute for tailored, one-to-one coaching: giving a sales rep individual feedback immediately following a sales conversation is the fastest path to improvement. Without that feedback, your sales team will be stuck standing in place.

    AI finally makes it possible for sales organisations to increase the number of reps who are meeting and exceeding quota. The only question is: will your team lead the way or be left behind?

    Dan Behrman

    Dan Behrman serves as the Senior Product Marketing Manager for AI, Analytics, Platform, and Security at Highspot. With over 15 years of experience in product marketing, product management, and engineering, he creates, delivers, and tells the story of solutions that enhance the lives of millions of users.

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