A Conversation With Doug Davidoff Part I: Understanding and Optimizing the Concept of Sales Playbooks

By: Teresa Weirich

December 14, 2018

Doug Davidoff, Founder & CEO, Imagine Business Development

It’s rare to find a sales professional who actually grew up with a goal to be in sales, but Doug Davidoff is one of those individuals. The founder and CEO of Imagine Business Development, a playbook-focused customer acquisition platform, knew from an early age that sales was the right path for him.

“I grew up in an entrepreneurial family and knew that the only way to grow a business is to sell a product or service,” Doug said. “Also, I was never really good at following rules and wanted a career where I could operate on my own terms. Sales is a great place to actually break the rules and work on your own timeline.”

After spending eight years at Merrill Lynch as a Wealth Management Advisor, Doug started Imagine Business Development in 2004 to address the growing need of targeted customer acquisition management. As a Hubspot Platinum Partner, Imagine Business Development began working with Costello to optimize playbook management and help customers create scalable and sustainable sales plans.

As a true sales thought leader, Doug has a wealth of knowledge and insight about sales playbooks and how teams can optimize their productivity. We hope you enjoy part I of this two-part series of our extensive conversation with Doug!

What is your personal definition of a sales playbook?

A play is a series of orchestrated actions taken by one or more people contextually in a situation. A playbook is a series of these plays, encapsulated to manage the entire sales process, from generating a lead to qualifying an SQL to close and ultimately handing off to customer success.

As a team, we’ve analyzed over 150 playbooks in the last year, and 98% of them are missing one critical piece: they don’t have actual plays! Most teams are working with what comes down to a single play. It’s often the manifestation of their sales process or how their sales pipeline is structured.

Some typical signs of a single-play playbook include objection books, FAQ sections, and battle cards. Unless you’re selling only the simplest of products, you’re going to need more options. You’re going to be talking to different personas, in different situations, and potentially conducting months of conversations. You’ll need more than FAQs.

What are some of the different ‘plays’ your team runs?

We’ve designed plays that run from the generating the first conversation to handing a new customer over to our customer success team. For example, given the nature of how our customers buy, we need to create multiple conversation points, often to just get the sale started. So we have a wide variety of ‘Reason to Talk’ plays. These are creative ways to enter into meaningful discussions with prospects. So, for example, we’ll run a play where we feature a prospect conversation on our blog. We legitimately want to tell their story, regardless of if the partnership pans out or not. It’s all about having a good conversation that matters to both sides. If the conversation continues, it’s a great first step in the sales process.

Other early plays include the ‘Question of the Month’ play where we research prospects and ask them a probing industry-specific question. This can turn into a conversation that prompts introducing products and solutions, and it also helps influence our long-term content calendar from a thought leadership perspective. These question-based plays also help to put our SDRs in what I like to call a position of ‘rehearsed authority’. When a rep is calling a prospect offering insight and education, it may sound purely consultative but it is actually a well-realized, scalable sales play.

How do playbooks impact different parts of the sales process?

The only two clearly defined points in most sales processes are the beginning and the end. The middle is full of confusion and frustration for both reps and prospects. Reps regularly make the mistake of going too far too fast. It’s important to clearly separate out milestones, such as:

  • Defining the game plan and intent of the sale
  • Defining the market and customer
  • Introducing messaging, stories, and context
  • Engaging with leads throughout the sales process

At Imagine Business Development, we truly run our sales plays like a sports play, with 20-yard line and Red Zone references. This helps drive context and really articulate the importance of each step in the process.

For example, I was recently watching the Rams playing the Packers. It was late in the game and on a third down play, Todd Gurley had an open lane to the end zone. He could have walked in the end zone and padded his stats, but instead, he pulled back and fell. He knew the real intent of the play was to run the clock. Reps need to do the same thing and think about the intent of sales conversations in a long-term context. The sales process becomes a play-by-play collection of actions so nothing is pushed past a point of no return.

What metrics can be assigned to different sales plays?

Of course, everyone wants to be a closer to ring the proverbial bell. But there are other milestones that can be tracked throughout the sales process, and plays help to connect these steps to different metrics. Optimizing and understanding the sales process as a collection of plays helps establish and manage these metrics. Our team actually relies on Costello to institutionalize these metrics. The activities at the end of every play transfer metrics into our CRM, which allow us to understand the success of an individual play.

How can teams optimize their use of sales playbooks?

One of the core components of Imagine is that we want to make growth practical, sustainable, and scalable. We want to put growth-focused people in a position where they can understand what they need to do to drive results. I’ve been involved with the creation of playbooks for more than two decades and can say that the reason most playbooks don’t work is that they’re not built to actually be used. If I’m going to ask a rep to change how they’ve done business on a daily basis for years, it better be a consistent change. I can’t just send them a PDF that is discussed once and ignored down the line.

Instead of trying to bring a salesperson to a playbook, create your playbooks with sales reps in mind. Our playbooks previously only orchestrated the beginning and end of calls and meetings, but reps truly need guidance in the middle. Our partnership with Costello enables us to map out entire aspects of the sales process and understand how people begin to engage with our products to really put our reps in a place where they can do what they do best: talk with and listen to customers.

The fundamental flaw in a sales play is that reps tend to forget there is a customer on the other end. Just like in sports, teams with good playbooks and good coaching staff improve through games and throughout the season. A good playbook puts you in a position to win, and Costello allows us to bring this success to reps without having to make them panic or stutter step. They’re able to just do it.

Did you like our Part I chat with Doug? Stay tuned for Part II!


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    Teresa Weirich

Ready to Learn More?

For more information on best practices of great sales leaders, check out the Costello resources below. If you’d like to see Costello in action, request a personalized demo of our real-time sales playbook software.

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