The Future of AI Coaching for Revenue Teams

As revenue leaders, we're witnessing a fundamental shift in how we coach and develop our teams. As we integrate these new technologies, critical questions emerge: Can AI truly replace human coaching? What separates effective AI coaching from ineffective tools? And can we trust automated systems to evaluate our most important conversations?

As VP of Revenue at Demodesk, I've had the opportunity to observe and implement AI coaching tools across our SDR, sales, and customer success teams. Through this experience, I've developed clear perspectives on where AI excels, where it falls short, and how to strategically leverage it alongside human coaching for maximum impact.

Establishing a systematic coaching process is essential to leading a successful team. When a comprehensive structure is created, it builds a foundation for a more prepared and effective sales team. This enablement should filter from the top down — the more coaches can feel prepared, the more sales reps can feel equipped to succeed.

As former VP of Revenue here at Demodesk, I was the sales leader for multiple departments including the SDR, sales, and customer success teams. As the leader and coach for these teams, I have to consistently check in to ensure that I am setting everyone up for success in the best possible way. I typically ask myself the following questions:

• How can I enable my team to ramp up efficiently and find success quickly?
• How can I ensure that they improve every day?
• What are the systems I need to put in place to promote this improvement?
• What are the coaching mechanisms that are working and what needs to be fixed?
• Importantly, how can I make sure people are enjoying their job?

In a webinar called World Class Coaching, hosted by Modern Sales Pros (check it out here!). In this conversation, along with Caroline Bray of Iterable, we talked about all facets of coaching a sales team and the importance of establishing an overall coaching culture throughout the entire organization.

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How to create a coaching structure

Where to start

I like to begin by focusing on the people and then creating a process around them. People need to have a willingness to be coached and to coach others. This is all about having the right mental mindset, which means it actually starts during the hiring process. Therefore, it is essential to create a hiring framework where you ask the right questions — this will ensure you find the most suitable fit for your team.

Once you have the right people in place, you can begin to build a personalized sales and coaching process. Figure out what the “North Star” is for your company and create a system around that focal point. Then determine which tools you can utilize to implement your blueprint.

How technology can help

Technology is a great tool to help build your coaching strategy. Automated coaching software is your friend when it comes to adequately preparing your reps. Ask yourself, what type or piece of technology can I leverage to best enable my reps? Automated coaching tools can range from AI-based conversation feedback to centralized battle cards to video practicing capabilities. Utilize the best technology for your team where it’s most essential for their success.

‍Automation also enables documentation consistency throughout the sales process — crucial for when you need to compile CRM data. Implementing automatic input systems will eliminate the time spent performing these administrative tasks. This gives sales reps the space to focus on the job you originally hired them to do.

For example — with Demodesk, information can be entered directly into the rep’s playbook throughout a meeting. Once the call has ended, that data is funneled into our CRM with one click. Investing in automation software helps to implement a thorough sales process and enhance your ability to coach the team.

As much as technology can be helpful, it’s important to remember to create a sales system first, then incorporate the automated coaching tools as a way to help streamline the process.

Where to incorporate coaching

Once you have your coaching framework created, you can begin to create space for incorporating your methods. Here are some ways you can integrate your coaching strategy:

Onboarding

During the onboarding process, quality coaching is all about reducing ramp time and getting reps active in the selling process as quickly as possible. To do this, you first need to understand your own expectations and goals for their progress. Ask yourself the following questions:

• What are your expectations for their first few months?

Create a clear 30-60-90 onboarding plan so you have a guidepost for your expectations — and a way to tangibly measure their progress. Don’t forget to share this plan with the rep as well! They need to know what is expected of them as they move through their first few months.

• How can I enable them throughout the process?

Determine where you can help ensure their success. Which tools can you use? Is the system in place working for them or can it be adjusted according to what they need? Every sales rep learns differently, so be logistical about each individual onboarding experience.

For me personally, Demodesk is a great example of how to successfully onboard new hires. I know that a new rep can walk in the door on their first day and have all the information they need in one place. They can be fully equipped for their first client-facing meeting, which means they can hit the ground running faster.

Implementing a mentorship program can also enhance the onboarding process. Offering peer assessment and coaching opportunities is valuable for both parties — it encourages the overall value of feedback and self-improvement from the very start.

Shadowing

As a sales leader, you will want to find areas where you can increase visibility. This is a necessity for both you and the sales rep as it instills clarity and communication. One way to achieve this is by shadowing meetings. Shadowing creates an opportunity to observe the sales process in action and provide direct coaching feedback. As a result, you can have more transparent conversations with your sales reps about how to adapt the process and where they feel they could use more assistance.

‍Shadowing is also a great way to see what collateral is being shared across the team — discovering firsthand if the narrative that has been put in place is actually working.

Pipeline meetings

Through shadowing, you already have direct knowledge of meeting details to approach pipeline conversations with more understanding and awareness.

In addition, utilizing data can assist in painting the overall picture. These metrics can help determine where the gaps are within the process — then, importantly, share these findings with your reps.

Transparency is the only way your team can make changes — without the ability to self-assess, they won’t be able to improve. Instead, these conversations can be an open discussion about the sales process. Is our content working? Is it engaging? Where can we get better?

This is another example of where automation can be a helpful coaching tool. For instance, Demodesk measures customer engagement in real-time. These types of in-depth analytics are essential for reassessing my coaching strategies and our sales process overall.

Career development

One of the best parts of coaching is helping sales reps grow to their full potential. To achieve this goal, create a career development plan that coexists with your coaching structure.

Have open and honest conversations with the reps about their goals and then coach to their specific objectives. Encourage them to take on projects or other opportunities that align with their ambitions and then coach them through their experience.

Effective coaching tips

Coach to one aspect

You can’t fix everything at once (though you might want to!). Instead, focus on the highest impact issue and coach to that problem. Observe their development and then move on to the next issue. It may be a slower process, but it will have greater lasting effects for the rep and your team overall.

Create clear competencies

Transparent and direct expectations are key to a successful team. Everyone should have a clear understanding of how to thrive in their role. Being a coach means helping them determine the management of their day — what are the most important tasks and how to best complete them with efficiency.

Stay consistent

Coaching is the easiest task to drop when your schedule becomes overloaded. However, staying consistent with your coaching is fundamental if you want to lead a successful sales organization. Even during those busy periods, be sure to own the structure you have created and ensure that all leaders are leaning into the process.

How to set up new sales managers for success

Transparency

I think that one of the most difficult aspects of moving from a sales rep role to a sales manager role is understanding that it’s a completely different type of position. Becoming a sales manager means you are working in people management, not number management. And that is a big shift! By sharing these distinctions with your new sales managers, you are starting them off with a clear understanding of what lies ahead for them.

Don’t be afraid to ask for assistance

Something I wish I had done earlier was lean on other coaches in my position. Encourage your new managers to join a leadership organization and utilize outside networking for assistance. Peers are a substantial resource for information, advice, and feedback. New managers aren’t expected to know everything right out of the gate, so other sales leaders can be some of the best educators.

Coaching across leadership teams

Create a connective string across the other leadership teams at your company. Instill a coaching culture environment and unite your managers under this principle. Sales leaders can often feel overwhelmed and left out on their own when it comes to coaching their team, so enforce the importance of coaching across all leadership. This creates a more unified and supportive system within the company.‍

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AI Coaching vs Human Coaching: Which Is More Effective?

The question isn't which is more effective—it's how they work together most effectively.

The Strengths of AI Coaching

AI coaching excels at scale, consistency, and immediacy. Here's where AI demonstrates clear advantages:

Instant feedback delivery. AI can analyze a sales call and provide feedback within minutes, while human coaches might need days to review recordings and schedule follow-up sessions. This immediacy means reps can course-correct in real-time, applying insights to their very next conversation.

Complete coverage. As a sales leader, I can't shadow every meeting. Even with the best intentions, human coaches can typically review only a small percentage of team calls. AI coaching systems can analyze 100% of conversations, ensuring no rep goes without feedback and no coaching opportunity is missed.

Objective consistency. Human coaches, despite their best efforts, bring subjective biases to evaluations. AI applies the same criteria to every call, eliminating favoritism and ensuring fair assessment across the entire team. This consistency is particularly valuable when coaching larger teams or maintaining standards across multiple managers.

Data-driven pattern recognition. AI can identify trends across hundreds of calls that would be impossible for humans to spot manually. It might notice that certain objection handling techniques correlate with higher close rates, or that specific talk-to-listen ratios predict better outcomes. These insights inform smarter coaching strategies.

The Irreplaceable Value of Human Coaching

Despite AI's capabilities, human coaching remains essential for several reasons:

Context and nuance. Human coaches understand the full context of a sales situation—the company dynamics, the political landscape of a deal, the personal circumstances affecting a rep's performance. This contextual awareness allows for coaching that goes beyond surface-level feedback to address root causes.

Emotional intelligence and motivation. Coaching isn't just about what you say—it's about how you say it. Human coaches can read emotional cues, adjust their approach based on a rep's mental state, and provide the encouragement or tough love that someone needs in a particular moment. They can sense when a rep is burning out before the metrics show it.

Career development and mentorship. As I mentioned in my coaching framework, helping reps reach their full potential requires understanding their long-term career goals and coaching to those specific objectives. This type of individualized career guidance requires human judgment and relationship building that AI cannot replicate.

Complex problem-solving. When a deal goes sideways or a rep faces a unique challenge, human coaches can draw on years of experience to suggest creative solutions. They can role-play difficult scenarios, share war stories that provide perspective, and help reps think strategically about complex situations.

The Hybrid Approach

The most effective coaching strategy leverages both AI and human capabilities in a complementary way. Here's how I structure this at Demodesk:

AI handles the foundational, high-volume coaching tasks—analyzing every call, identifying basic improvement areas, flagging concerning patterns, and providing immediate feedback on technique. This frees human coaches to focus on higher-value activities: having deep one-on-one conversations about career development, addressing complex performance issues, providing strategic guidance on major deals, and building the relationships that create psychological safety and trust.

Think of AI as your coaching assistant that never sleeps. It does the heavy lifting of reviewing all conversations and surfacing what needs attention. Human coaches then apply their judgment to determine what matters most and how to help each rep improve.

What Makes a Good AI Sales Coach?

Not all AI coaching tools are created equal. As I've evaluated and implemented various solutions, I've identified several characteristics that separate effective AI coaches from glorified call recording systems.

Accuracy in conversation analysis. This seems obvious, but many AI tools struggle with basic transcription accuracy, especially with industry jargon, accents, or poor audio quality. A good AI coach must correctly understand what was said before it can provide useful feedback. Test any tool thoroughly with your actual calls before committing.

Relevant and actionable feedback. Generic observations like "you should ask more questions" aren't helpful. Effective AI coaching provides specific, contextual feedback: "You missed an opportunity to explore the prospect's budget concerns at the 14:23 mark when they mentioned quarterly planning." The feedback should point to exact moments in the conversation and suggest concrete alternatives.

Customization to your sales methodology. Every company has a unique sales process and methodology. A good AI coach should align with your specific approach—whether that's MEDDIC, Challenger, solution selling, or your own framework. It should reinforce your language, your qualification criteria, and your deal stages, not impose a generic methodology.

Integration with your existing tech stack. AI coaching shouldn't create more administrative work. The best tools integrate seamlessly with your CRM, conversation intelligence platform, and other sales enablement systems. Information should flow automatically between systems, reducing manual data entry and ensuring coaches have a complete view of performance.

Focus on high-impact behaviors. Remember my coaching tip about focusing on one aspect at a time? Good AI coaches prioritize feedback the same way. Instead of overwhelming reps with twenty different improvement areas, they highlight the two or three changes that will have the most significant impact on outcomes.

Continuous learning and improvement. The AI should get smarter over time, learning from your team's successful calls and adapting to your specific business context. It should recognize that what works for enterprise deals might not work for SMB sales, and adjust its coaching accordingly.

Transparency in how it works. You should understand the logic behind the AI's recommendations. Black box systems that can't explain their reasoning are difficult to trust and improve. Look for tools that show you why they're making specific suggestions, allowing you to validate and refine the coaching criteria.

Balance between automation and human oversight. While AI can provide immediate feedback, there should be mechanisms for human coaches to review, approve, or override AI suggestions. The system should enhance human judgment, not replace it entirely.

Is Automated Call Scoring Reliable?

This is perhaps the most contentious question in AI sales coaching. The short answer: it depends entirely on how the scoring system is designed and implemented.

Where automated scoring succeeds:

Objective metrics. AI is excellent at measuring quantifiable elements of sales conversations. Talk-to-listen ratios, question frequency, filler word usage, speaking pace, monologue duration—these can be scored reliably and consistently by automated systems. These metrics provide valuable insights into conversation dynamics.

Keyword and topic tracking. AI can reliably identify whether key topics were covered during a call. Did the rep discuss ROI? Did they mention competitors? Did they uncover pain points? Automated systems excel at this type of checklist-based assessment, ensuring no critical element of your sales process is skipped.

Relative performance benchmarking. While the absolute score might be debatable, AI can effectively rank calls relative to each other. This allows you to identify your top performers' calls and understand what distinguishes them from average or struggling reps.

Compliance and risk detection. For industries with regulatory requirements, AI scoring reliably flags potential compliance issues, unauthorized discounting, or promises that could create legal exposure. This protective function has significant value beyond coaching.

Where automated scoring struggles:

Subtle communication nuances. AI has difficulty assessing soft skills like empathy, authenticity, or the ability to build rapport. It might score a call as excellent based on technique while missing that the prospect felt pressured or disconnected. These human elements often determine whether a deal actually closes.

Context-dependent quality. A great discovery call looks different from a great closing call, which looks different from a great renewal conversation. Effective scoring systems must account for these contextual differences, but many don't. They apply one-size-fits-all criteria that don't match the reality of where each conversation sits in the sales cycle.

Strategic decision quality. Did the rep make the right call when they chose not to push for a next meeting because they sensed the prospect needed more time? Should they have brought in technical support or handled objections themselves? These judgment calls require human assessment.

Relationship building over time. Sales isn't just about individual calls—it's about relationship development across multiple touchpoints. An automated system scoring a single conversation in isolation misses the broader relationship context that often determines deal outcomes.

Making automated scoring work:

Based on my experience implementing these systems, here's how to maximize the reliability of automated call scoring:

Define clear, specific criteria. Work with your best reps and coaches to identify the specific behaviors that correlate with success in your business. The more concrete and observable the criteria, the more reliably AI can assess them.

Customize scoring models for different scenarios. Create distinct scoring frameworks for different call types, deal stages, customer segments, and product lines. A prospecting call should be evaluated differently than an executive business review.

Combine AI scores with human validation. Use AI scoring as a first pass to surface calls worth reviewing, then have human coaches validate the scores and provide additional assessment. Review a random sample regularly to ensure the AI remains aligned with your standards.

Focus scores on improvement, not evaluation. Automated scores work best as coaching tools rather than performance management tools. Use them to identify learning opportunities and track progress over time, not as the primary metric for compensation or promotion decisions.

Continuously calibrate the system. Your sales process evolves, your product changes, your market shifts. Regularly review and update your scoring criteria to ensure the AI remains aligned with current best practices. Meet quarterly with your team to discuss whether the scoring system is helping or creating frustration.

Supplement with human-scored elements. For the aspects that AI struggles to assess—strategic thinking, relationship building, emotional intelligence—incorporate periodic human scoring. This creates a more complete picture of rep performance.

The Bottom Line on Reliability

Automated call scoring is reliable for what it's designed to measure—observable behaviors and conversation patterns. It becomes unreliable when we expect it to assess nuanced human interactions or replace human judgment entirely.

Think of automated scoring like a fitness tracker. It can reliably tell you how many steps you took and your heart rate, but it can't tell you if your workout form was good or if you should push harder tomorrow. You need both the data and human interpretation to improve effectively.

Building Your AI-Enhanced Coaching Strategy

As you integrate AI coaching into your revenue team, consider these principles:

Start with your coaching structure first. Don't let technology dictate your coaching approach. Define what great coaching looks like for your team, then find AI tools that support that vision. Technology should enhance your existing framework, not replace it.

Set clear expectations with your team. Be transparent about how AI coaching tools will be used, what's being measured, and how it affects them. Address concerns about surveillance or job security upfront. When reps understand that AI coaching is designed to help them improve, not catch them making mistakes, adoption increases significantly.

Train coaches on AI interpretation. Your managers need to understand how to use AI insights effectively. This includes knowing when to trust the AI, when to dig deeper, and how to have conversations with reps about AI-generated feedback without undermining their own coaching authority.

Measure what matters. Don't get distracted by vanity metrics. Focus your AI coaching on behaviors that actually correlate with revenue outcomes for your business. Continuously test and validate that the metrics you're tracking truly predict success.

Maintain the human connection. Even as you automate more coaching functions, protect time for genuine human connection. Schedule regular one-on-ones, create mentorship opportunities, and ensure that efficiency gains from AI translate into deeper, more impactful coaching conversations, not just fewer coaching hours.

The Road Ahead

The future of sales coaching isn't human versus AI—it's humans augmented by AI. The most successful revenue teams will be those that thoughtfully integrate both approaches, using AI to handle scale and consistency while preserving the human elements that truly develop people and drive performance.

As these technologies continue to evolve, we'll see AI coaches that better understand context, provide more nuanced feedback, and integrate more seamlessly into our workflows. But the fundamental truth remains: coaching is ultimately about human development. Technology can enhance that process, but it cannot replace the relationship, trust, and mentorship that effective coaching requires.

The question for revenue leaders isn't whether to adopt AI coaching—it's how to do so in a way that genuinely serves your team's development and your company's growth. By approaching AI coaching with clear strategy, realistic expectations, and a commitment to the human side of leadership, you can build a coaching culture that leverages the best of both worlds.

As I continue to refine our coaching processes at Demodesk, I'm constantly reminded that our success comes from people who feel supported, equipped, and motivated to improve every day. Whether that support comes from a manager, a peer, or an AI tool matters less than ensuring it's consistent, relevant, and genuinely helpful. That's what world-class coaching looks like—and that's the future we should be building.

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