In this episode of The Revenue Leadership Podcast, I had the pleasure of sitting down with Kevin “KD” Dorsey, a true veteran in the world of sales leadership and startup growth. With 13 years of experience building startup sales teams — and a couple of unicorns under his belt — KD brings a wealth of knowledge to our conversation about optimizing sales playbooks.
Today, KD wears two hats: CRO at finally, a finance automation platform for SMB, and founder and CEO of Sales Leadership Accelerator, a training program for current and aspiring sales leaders.
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What I love about KD is his passion for serving entrepreneurs and small business owners. He sees them as the backbone of our economy and is dedicated to providing the tools and support they need to succeed. His experience spans from early stage startup to late stage growth with a ton of advisory and consulting thrown in, giving him a unique 360-degree view of what it takes to build and scale successful revenue organizations.
In our conversation, KD shares invaluable insight on how to create effective playbooks, drive adoption, keep them fresh, and ensure they have an impact on performance.
1. Master the 5 Ps of sales playbooks
At the heart of KD’s approach is his “5 Ps” framework, which provides a comprehensive structure for building effective sales strategies and processes. Here’s the quick breakdown:
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People: Define standards of excellence, virtues and values, and expectations for each role, including goal setting, quotas, and pathways for promotion.
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Prospect: Detail what success looks like for your buyers, define personas, and understand key market trends and terms to truly grasp who you’re selling to.
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Problem: Identify specific problems you solve for each persona, creating a buyer matrix that explains not just what problems exist, but why they exist.
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Process: Outline day-to-day operations, including sales stages, criteria, qualification processes, scripting, scorecards, and issue diagnosis checklists. Big checklist guy.
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Product: Connect your product to the other four Ps, focusing on how it aligns with prospects and solves their problems rather than just what it does.
2. Document, document, document
Sales leaders throw the term “playbook” frequently, yet they’re often misunderstood or poorly implemented. KD’s definition is simple: A playbook is a documented set of best practices and “What Good Looks Like” — what he calls WGLL (pronounced “wiggle”). While it takes time to develop, a documented playbook is crucial for scalability, onboarding efficiency, performance consistency, and continuous improvement. “You already know this stuff. It’s in your head, you just need to put it down,” KD says. Defining and documenting WGLL transforms abstract knowledge into a concrete, actionable playbook that drives team success.
3. No leader works alone
Playbook creation should be a collaborative effort. Just 90 days into his new role, KD has made significant progress on his playbook by involving managers and team members in the process. He meets weekly with other revenue leaders to build out elements of the playbook and taps into the organization’s Slack channel, communicating what he’s working on and inviting interested parties to contribute. A cooperative approach ensures the playbook contains realistic strategies and gains widespread acceptance. This was one of my favourite takeaways from the conversation.
4. Think about volume or volume
Yes, you read that right. KD offers this approach to prioritizing playbook development: consider “volume or volume” — is the issue loud or does it happen often? Don’t focus solely on loud problems that rarely occur; prioritize issues that are frequent. To guide this prioritization, tie each problem to a specific metric and focus on the worst-performing areas first. KD likens leadership to “controlling the burns,” where you need to address the most impactful and frequent issues rather than being distracted by isolated (albeit noisy) fires. This strategy ensures that your playbook development efforts yield the highest return on investment by tackling the most pressing and recurring challenges in your sales process.
5. Don’t just ask, observe
Most people struggle to articulate what makes them successful, making observation critical for identifying true best practices. Watch top performers in action, whether through screen recordings or in-person shadowing, to uncover the nuanced behaviors and skills that drive their success. By focusing on what people actually do, not what they say they do, your playbooks will reflect real-world, replicable practices that can elevate the entire team’s performance.
6. Stop letting playbooks gather dust
Playbooks are meant to be practiced, not just read. Make them a central part of daily operations, from training and coaching sessions to one-on-ones. Don’t just answer reps’ questions; point them to the relevant section of the playbook. KD wrote a great post about his team practicing his scripting and getting certified recently.
Keep the playbook fresh by updating it regularly with new learnings and insights — then sharing those changes with the team. KD holds a quarterly “studying greatness” exercise, where managers identify and study top performers in specific metrics or processes, incorporating their best practices into the playbook. Actively using, referencing, and updating the playbook ensures it remains a living document that continually drives performance.
7. Measure adherence and success rigorously
Gauging the use and success of your playbook seems complicated, but KD argues it’s simple: iIf someone’s performance is below par, they’re likely not running the plays laid out in the playbook. Create an issue diagnosis checklist for every metric to quickly identify where breakdowns are happening. Remember: checklist guy.
8. Lead with empathy and individuality
Our lightning round left us with this gem. True leadership isn’t about molding team members into carbon copies of yourself, but about making them better versions of themselves. KD’s advice for leaders is, “Don’t turn people into you.” Recognize and respect individual differences — and constantly practice the mantra “I am not you, you are not me, we are not them, they are not us.” This mindset fosters empathy and understanding to use the diverse strengths of your team members rather than trying to fit everyone into the same mold.
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