Five Tips to Transform Your Sales Coaching and Increase Revenue

By Ariel Hitron, CEO, Second Nature AI
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Incorporating great sales coaching can boost your company’s revenue and increase your sales staff’s productivity. According to a 2021 Second Nature Sales Coaching Survey, 96% of respondents either agreed or strongly agreed that effective sales coaching made a big difference in the performance of their salespeople. Sometimes, though, sales coaching is not as effective as it can be.

Ad hoc is not the best approach

Unfortunately, sales coaching often takes place as part of a weekly pipeline discussion, where a manager may discuss strategies for bringing the deal to the next stage. But this approach fails to look at the big picture and, as a result, can only take the company forward in baby steps.

Many sales managers are more comfortable with this ad hoc approach – after all, that’s probably how they were coached when they were reps. However, an effective sales coaching strategy should be a vital part of your company’s business strategy. Otherwise, you could be left lagging behind your competitors.



The biggest factor when developing a strong sales coaching program is to look at your company’s strategic goals. For example, do you want to increase the pipeline for a particular market or expand into new markets? By determining the areas on which you want to focus in the long term, you can structure your sales coaching program on those particular goals.

Once you have determined your goals, use company data to help identify the best ways to move forward. You can dig into the data in your customer relationship management system to help determine your sales team’s weak spots.

For example, if you see from your CRM data that only 10% of your reps are generating deals for your newest product – and your goal is to increase revenue for that product – your most likely course of action would be to coach the other 90% on how to sell that new product. You might even break that down into several structured practice-and-coaching sessions around the features and benefits of the product, customer success stories, and how to differentiate it from the competition.

AI sales coaching platforms like Second Nature can also be a rich source of data. Second Nature’s AI sales coach – named Jenny – grades reps on the topics they covered and their selling style in simulated conversations they hold with her. These can be crucial inputs for your coaching plan.


Another important aspect of a strong sales coaching strategy is to make sure to set aside enough time for the process. About 37% of Second Nature survey respondents allocated 15–30 minutes toward each sales coaching session, while another 33% devoted 30–60 minutes. From our experience, short sessions that take place more often are most effective for ensuring salespeople remember what they learned.

We strongly recommend that companies incorporate sales coaching as a regular part of every salesperson’s weekly schedule, in addition to having it as part of your annual sales kickoff and quarterly business reviews.

Just like any athlete, time spent in the batting cages or on the driving range with some feedback from a coach can help improve a salesperson’s game. Being able to spin up a practice-and-coaching session at a moment’s notice with an AI sales coaching solution encourages your salespeople to actually put in the time on improving their skills.


Just like with the batting cage or driving range analogy, creating a safe space for your sales staff to practice is important. This can be in front of a mirror, in front of a webcam, or even just recording voice notes and listening back to them. However, each of these examples are just monologues – while real, live sales conversations are typically dialogues. At least we hope so!

Conversation practice is a crucial part of the sales coaching process, and salespeople should be engaging in it on a regular basis either through one-on-one role-plays with managers or peers, or through an AI practice tool. Our enterprise clients whose sales reps practice and receive coaching from our AI coach Jenny typically improve their results by 44% simply by practicing four times over the course of 30 minutes.

Where better to make a mistake when it comes to a sales call than in an environment devoid of risk and where failure can occur with no judgment?


There’s no substitute for working with a fantastic coach who really knows the material and can get the best from each salesperson. But whether it’s a member of your team – say an experienced sales manager – or someone you brought in from the outside, that coach’s time is limited. So scaling up a coaching program that’s 100% based on human coaches will be unnecessarily limiting.

Imagine if your salespeople could have unlimited practice time and feedback, and then could work one-on-one with the live sales coach you’ve selected, in exactly the area they need the most help, support, and feedback? This is the ideal scenario of blending an AI coach with a human one.

By practicing over and over with the AI coach, the sales rep can improve their sales conversations significantly. At the same time, their managers can then view the aggregated results of these practice sessions and zoom in to specific areas, giving their one-on-one coaching sessions much more focus. Managers can also listen to specific portions of practice sessions as needed, and focus their personal coaching efforts on the most impactful areas.


Gamification is a great way to boost salespeople’s engagement with the coaching process.

Zoom did an amazing job generating excitement and engagement with its sales coaching and certification strategy by turning it into a competition. Using Second Nature’s AI coaching tool, their sales teams were scored on various sales simulations, and the team with the highest score won the competition – and earned cool prizes.

Check Point Software had its thousands of salespeople practice conversations around new, advanced products, using Second Nature’s AI sales coaching software. As a result of switching to the structured, AI approach, the company saw a 3X increase in the number of exercises completed by each salesperson, along with a measurable improvement in sales productivity.

There are so many different topics on which a salesperson needs to be up to speed: We counted that, for one of our enterprise customers, a sales rep might need to have up to 300 different types of conversations with a prospect! The only way for reps to be prepared for such a scenario is to practice and be coached in an ongoing, well-planned way. One piece of this puzzle can be AI coaching from Second Nature.

As the Gartner analyst Dan Gottlieb wrote in his recent report, “Cool Vendors in Conversation Intelligence for B2B Sales”: “By relying on Second Nature’s Jenny to conduct role-play exercises, sales leaders can accelerate the rolling out of critical go-to-market changes across a hybrid workforce. The frontline manager preserves a significant amount of bandwidth for high-impact coaching behaviors, such as performance improvement and deal-level coaching.”

Coaching is crucial for salespeople. For this reason, so many winning organizations and companies use a combination of AI and traditional sales coaching as one of the many effective strategies in their arsenals.

Ariel Hitron is the co-founder and CEO of Second Nature AI, a SaaS solution that lets you scale up sales coaching, onboarding, and certification. It provides a “virtual role-play partner” that uses conversational AI to have actual discussions with sales reps, score them, and help them improve, so they can ace every sales call.