Want reps to engage with a sales playbook? Let them help build it.

Creating a sales playbook takes time and effort, but it’s only useful if the sales team sees it as a tool for driving success. If reps see areas for improvement but don’t feel empowered to suggest a change to their organization’s sales process, they might not feel compelled to lean on the playbook at all.

The key to driving engagement, sales leaders from local tech communities said, is employee ownership.

At freight brokerage company Arrive Logistics and database startup MongoDB, sales leaders said playbook development and refinement strategies revolve around feedback from reps at every level of the sales organization, as well as input from clients and cross-departmental stakeholders. Sometimes, they said the ideas of individual salespeople turn into team-wide implementations.

One tip to keep in mind, however, is that the work is never finished.

As sales strategies, products and industries evolve over time, sales teams should receive continuous training on each. Furthermore, any updates made to a sales team’s playbook should be piloted, rolled out and then tested long-term to better evaluate the efficacy of any strategy, sales leaders said. While some change is necessary, constant change becomes messy. 

What To Include In Your Sales Playbook:

  • Onboarding
  • Sales messaging and scripts 
  • A repository for cadences by persona and industry
  • Sales team alignment on a single sales methodology (i.e. Winning by Design, SPIN, etc.)
  • Best practices for every stage of the sales cycle



Phil Carlino, Head of Dental Sales, North America 

Phil Carlino

How do you format and deliver your sales playbook to the team? 

At Formlabs, we use a tool called TalentLMS for all new hire onboarding. This tool helps us get our new sales reps up to speed on the products we sell, the competitors we sell against, and the buyer persona within each individual vertical.

Within our sales team, there is a lot of group and interactive learning. The “playbook” is more of a guide that gives structure to our sales process. A lot of training for junior-level reps comes through coaching and development by managers and senior-level individual contributors. 

Just last week, my team had a half-day session on customer profiling, building a sales strategy and role-playing. This was a great way to take a step back and look at the big picture, while also helping one another improve fundamental sales skills.


How do you keep your playbook up to date, and when do you know it's time to make an update?

We use TalentLMS for all onboarding across sales, services and for some technical employees as well. Because we sell to such a wide range of customers from several different verticals, some training sessions are led by industry-specific specialists. For continued learning, we use this as a guide to help reps gain competency within different market segments and to better understand the competitive landscape and buyer personas.

I don’t think any Formlabs team has an ongoing formal playbook; as the team evolves, the training evolves. We’re not regimented to follow a playbook since they get outdated quickly and things in our space move so fast. Our team is adaptable to the evolving landscape, and most of our product-specific training and development comes from our product or marketing team.


"The best ideas come from the ground up, and we want to share those ideas.” 


How do you include your salespeople in the process of developing your playbook? 

The team is instrumental in developing and refining the training material. They’re either assigned, or they volunteer to tackle where there is a need. As an example, one topic we developed in our recent training session was how to use the CRM system better to automate outreach. It was developed by a sales rep and put into the playbook. All training doesn’t need to come from management. The best ideas come from the ground up, and we want to share those ideas. 



Tommy Deluca, VP of Sales

Tommy Deluca

How do you format and deliver your sales playbook to the team, and why? 

The evolution of PebblePost’s sales playbook is as follows: the content goes from my notebook to a shared Google Doc to a PowerPoint presentation that is eventually delivered to the team through one of our (now virtual) team meetings. 

This format allows us to foster collaborative thinking among both sales leaders and department heads, in order to align the sales playbook with our company goals and the PebblePost vision.

Rooted in a consultative sales approach, the PebblePost sales playbook is based on efficiency and streamlined tactics for driving new business and maintaining existing partnerships. With that said, we utilize a number of technologies and tools to keep us organized, focused and over-communicative, including Salesforce, Google Hangouts, Outreach.io, SimilarWeb, Jira, Confluence and Slack.


What processes do you have in place for keeping your playbook up to date? 

Any good playbook needs to evolve as a business evolves. Although our mission and our company values remain consistent, we adapt alongside market trends and partner feedback, continually striving to be leaders in digital to direct mail space. For example, we spend a lot of our time focused on customer segmentation and identifying which types of brands could most benefit from PebblePost, particularly as our platform evolves and expands. 

Doing so changes our prospecting and outreach strategies and subsequently alters our playbook. In regard to processes, we listen to what our brand partners are saying about our products and processes. We listen to what our board of directors is seeing in the marketplace. And we listen to our employees regarding how we can improve both internally and externally. You’ll know it’s time to tweak your playbook when you listen well enough to see that your current plan is outdated. 


"You’ll know it’s time to tweak your playbook when you listen well enough to see that your current plan is outdated.’’ 


How do you include your salespeople in the process of developing your playbook? 

Keeping salespeople involved in the process is essential. They are the ones using the playbook. At PebblePost, we strive to foster a culture of learning and curiosity. Feedback from our salespeople has prompted a redesign of our sales onboarding program for new hires. Additionally, it sparked several sales product trainings, as well as an improved resource library for important content and collateral.

For me, a playbook is a guideline for best practices. It cannot be a rigorous doctrine that requires exhaustive step-by-step instructions. It’s more important that sellers are given the proper framework and the autonomy to make it their own. Everyone’s selling style is different. The playbook should be used as a blueprint for success, but it is not the only design that leads to positive results. 

Recently, one seller changed our campaign proposal process, resulting in a stronger deal and a happier client. It was a brilliant tactic that was consistent with our consultative directive. We have since adopted the new process into our playbook. Flexibility, collaboration and teamwork are vital to ensuring our playbook remains relevant and effective in a fast-paced marketplace. 

Find out who's hiring.
See all Sales jobs at top tech companies & startups
View 3812 Jobs


Redgate Software

Kaulana Shum, Sales Manager

Kaulana Shum

Sales Manager Kaulana Shum believes in the power of sales playbooks to help reps reach their targets, but stressed that building them is a collaborative and ongoing process. While writing a playbook for Redgate Software, a company that develops tools for Microsoft Data Platform, he asked his team what they specifically wanted to see in the process to help them win. 


How do you format and deliver your sales playbook to the team?

I’ve experimented heavily with playbooks and found that it’s important to determine beforehand what you want to accomplish. For some, it’s best practices and messaging for their sales reps. For others, the goal is to help new hires get up and running as fast as possible. For me, I believe that if a rep reads through the playbook and uses it to learn and execute, then they will hit their target.  

I now save playbooks as Google docs so I can update them as often as I want, and the reps can always access the latest versions.


How do you keep playbooks up to date, and when do you know it’s time to change?

At some point, you’ll feel like the playbook is complete, so you push it aside and let it sit. I recommend fighting against this tendency because the playbook should be a living document that is constantly updated. If a sales team doesn’t adapt and optimize, then they’re getting outclassed by their competition. With that said, my teams have always been very proactive in running tests to see if we can improve our success rate on the phone or via email, and we’ll record the results in the playbook.

With help from sales ops, I also track conversion rates from stage to stage, and see how we can tweak the sales process. For example, if we have a low conversion rate from the point-of-contact stage to the closed or won stage, we spend some time examining and updating the strategy and methodology in the playbook.


How do you include your salespeople in the process of developing your playbook?

One of the best tactics I’ve used in creating a playbook is to spread the burden to my team and invite them to contribute on a topic they’re knowledgeable about. Sales reps then associate that skill as part of their identity and self-image. The message they get is that they are a great LinkedIn sales prospector, or they run great demos. When writing about the topic, they tend to deconstruct every step in their process, making them even more deliberate in this skill.

The hardest lesson I learned after rolling out a playbook to a team occurred when I asked for feedback and only got silence. It reminded me that adoption is a process and sales reps aren’t exactly clamoring for things to read in between emails, demos and dealing with legal. Instead, I now ask, “What do you want to see in this playbook that will help you win?” Then we work together to get their recommendations into the playbook.

Adoption soars when everybody participates. It becomes “their” playbook, not “their boss’s” playbook.



Paul Cohen, National Director

Paul Cohen

National Director Paul Cohen said his sales team’s main focus is getting their broker clients to start using the company’s product, real estate platform CREXi. Though the objective may sound simple, Cohen said the sales team uses several specialized playbooks to help close every kind of deal. Outside of the playbooks, video courses and product demonstrations keep the team informed, engaged and ready to provide feedback on the process. 


How do you format and deliver your sales playbook to the team?

We actually have several playbooks for our sales team: a BDR playbook, an SDR playbook, an AE playbook, a territory manager playbook, a regional director playbook, a conferences playbook, and so on. We don’t hire salespeople; we hire consultants. We don’t sell CREXi. Instead, we show our commercial real estate broker clients how to use CREXi to sell and lease their listings. This subtle shift in thinking makes all the difference in our strategy. We simply need to show our clients how to use the tools we provide. From there, we get them on a demo.

Many on our sales team come from a commercial real estate (CRE) background, so their working expertise plays into our conversations with brokers and how we address their real-world pain points. On the other side of the coin, much of our personnel come from the SaaS world who recognize CREXi’s unique position in the CRE market. To train our non-real estate employees, we give them a crash course in CRE. This video course is led by dynamic in-house instructors who break down everything CRE into simple, bite-sized chunks.


How do you keep playbooks up to date, and when do you know it’s time to change?

Our playbooks are living documents that grow and morph as new processes and product features are developed. Since our platform is evolving on a biweekly basis, keeping the team up to date on new tools is vital. We hold weekly Zoom product meetings led by our product development team. The product is unveiled, feedback is sought and changes make their way into the corresponding sales playbook.

It’s a very open and collaborative process with the sales team providing feedback from the field and our engineering team making it possible. 


How do you include your salespeople in the process of developing your playbook? 

We maintain our playbooks in SharePoint, where any member of the sales team can make a recommendation. In a recent sales call, several sales team members shared that they didn’t think their product suggestions were being heard or prioritized appropriately. 

As a result, the playbook was modified to include a monthly sales and product “town hall,” where the territory manager shared survey results from the entire sales team, which prioritized the most impactful upgrades of our platform based upon client feedback. Many of these changes were quick yet impactful, such as adding new search filters for property types on the platform, like “cannabis” and “religious facilities.”

The open dialogue between product and sales is essential to equipping our broker clients with the best CRE tools possible.



Tom Straszewski, SVP Sales and Business Development

Tom Straszewski

SVP of Sales Tom Straszewski said a sales playbook’s purpose is to ensure reps have the tools they need to offer excellent customer service to their clients at crowdsourced shopping platform Slickdeals. His team continually analyzes internal activity data and updates the playbook from there.  


How do you format and deliver your sales playbook to the team? 

Sales playbooks are important tools to help educate our team and are designed to assure our team is offering best-in-class customer service to our clients. At Slickdeals, we host ongoing internal meetings and training sessions to ensure that all members of our team are aligned on advertising solution presentations and sales processes. These meetings also allow space and time for team members to ask questions and workshop conversations they may be having with clients. 

Additionally, we use different sales pipelines that are precisely mapped for each type of revenue-generating initiative across several categories, and we enable automation to assign tasks and route business. This guides the entire sales process for our team.


How do you keep playbooks up to date, and when do you know it’s time to change?

We are continually analyzing our sales efforts and make regular updates to optimize our playbooks based on internal activity data. We have found that a powerful, automated and user-friendly sales CRM that can also integrate with marketing efforts provides a holistic and accessible view into real-time performance. We use HubSpot for our sales CRM and B2B marketing efforts. 

Typically, we elect to make changes when we see drastic swings or differences in performance between various content or tactics. Our approach would probably be best described as “continual A/B testing” with a lot of trial and error.


How do you include your salespeople in the process of developing your playbook? 

Our salespeople play an essential role in helping define our sales processes and playbooks. For most of Slickdeals’ history, we did not use any kind of CRM tool, so the experiences of our salespeople and account managers were foundational in the initial integration. Likewise, we continue to solicit feedback from our clients.

Recently, we’ve invested in specialized case studies and abbreviated collateral conducive to quickly sharing information with peers, per the team’s request. Another recent example would be an adjustment to the hand-off process between the sales team and the account managers, which streamlines the onboarding process based on client persona and lead score. 


Caliper Foods

Jolene Jacobs, General Manager of Caliper Ingredients

Jolene Jacobs

“Salespeople should always be involved in the development of the playbook,” said Jolene Jacobs, GM of caliper ingredients at Caliper Foods. “They are closest to the customers and should be bringing the insights from the street into the organization.”

The leader at the soluble cannabinoids company shared the importance of keeping salespeople involved in optimizing the playbooks they use.


How do you format and deliver your sales playbook to the team, and why? 

The foundation of the sales playbook should stem from company objectives. Once a foundational company roadmap is set, it allows the sales team to format their playbook to support those goals. The link between the two is critical to success and also dovetails into performance. Too often there’s a disconnect between the sales playbook and the company objectives, and it’s something that can be easily avoided. 

I think of formatting our playbook in a few sections. First, we identify the categories we want to play in, like beverage, confection or skin care. Then, we determine our points of differentiation that will enable us to win within those categories. But it’s also necessary to highlight points of parity so that prospects see the full picture of what our business can offer. And we need to identify key customers within the “where to play” categories we chose. It is important to differentiate the audience based on complexity or “ability to convert.’’


"Provide salespeople with an open forum where they are encouraged to challenge the status quo.”


What processes do you have for keeping your playbook up to date? 

The playbook should be something that is referred to on an ongoing basis to ensure that progress is being made. It also makes certain that there have been no major shifts in the industry that would force a need to pivot. And avoid pivoting unnecessarily. 

It is important to continue to make the critical phases of the process as lean as possible while not allowing “squirrels” to distract teams from the strategy. A playbook should always be evolving. As a team works the playbook they should be encouraged to find better ways to move customers through the sales process while supporting clients. I like to reexamine the playbook yearly, and I am a fan of monthly check-ins or business updates to measure progress.


How do you include your salespeople in the process of developing your playbook?

Handing a team a playbook and simply telling them to go execute leaves a lot of talent on the table. Provide salespeople with an open forum where they are encouraged to challenge the status quo or voice a new way to approach an idea that was turned down. This creates an environment of solution providers. There are always going to be problems to solve, and it is OK to bring them up. But when surfacing an issue, I encourage my team to proactively come with a solution or a starting point that may lead to one.

And recognize people’s strengths. A great sales team is made up of different personalities and skill sets. So one person may be a better fit for a certain customer or company personality. Balance that individuality with knowing when to team sell. 



Ryan Pryor, Senior VP of Global Sales

Ryan Pryor

Continuous knowledge sharing plays a vital role in how the sales team at objectives and key results platform Gtmhub keeps their playbook in winning form. Senior VP of Global Sales Ryan Pryor said weekly teamwide learning sessions keep sales best practices top of mind while a data-sharing platform keeps information accessible to everyone.


How do you format and deliver your sales playbook to the team, and why? 

The initial delivery of the sales playbook, or iterations on it, are presented and explained in a group setting. Typically, we set up team training in a lunch and learn, presenting to the entire global sales team. This environment allows the team to learn and grow as a unit, not disproportionately over different regions. Reinforcement of the central concepts and ideas are then taught weekly in a workshop where team members role-play and practice with one another. 

From a technology perspective, we use Confluence, which is a workspace where teams can create, collaborate and organize all the work in one place. It’s an open, connected structure that allows information to flow freely among everyone in sales and the broader organization with integrations with other data repositories.


"There is always room for iteration to provide a more powerful buyer journey.”


What processes do you have for keeping your playbook up to date? 

Procedural obstacles that impact the sales team become apparent during customer calls, one-to-ones, continuous learning and deal strategy sessions. When situations arise that are not one-off scenarios, we make it a priority to change. Furthermore, as we refine our global go-to-market strategy, focus is put on what processes need updating to empower our sales professionals. Our fundamental value-based sales motion supports and aligns with our direction, but there is always room for iteration to provide a more powerful buyer journey.


How do you include your salespeople in the process of developing your playbook?

I solicit feedback and suggestions from the sales team, then enable them to make the necessary changes. Recently, we deployed a persona-based account executive outbound channel focused on strategic accounts in the given territories. As part of that deployment, we needed the right approach to personalize our outreach to senior leaders at these high-profile companies. Initially, I proposed a methodology and reached out to the team to get their opinions. One of our sales reps proposed a different way of going about it and the reasons why. The team voted and chose the AE’s solution, who then built out the process and trained the team — and produced instant results.

Find out who's hiring.
See all Sales jobs at top tech companies & startups
View 3812 Jobs


Arrive Logistics

Duke Begy, Executive VP of Business Development

Duke Begy

The sales playbook at freight brokerage Arrive Logistics is optimized for reps through continual feedback. Executive VP of Business Development Duke Begy said there are multiple channels for salespeople, stakeholders and customers to voice their concerns and suggestions. Sales leaders then make changes to their team processes based on common threads in feedback. 


How do you format and deliver your sales playbook to the team, and why? 

Our sales playbook starts with our learning and development program. We share and leverage scripts and slide decks to train our sales force, but we are also focused on mentoring, shadowing and hands-on learning. On their first day, sales reps start real-world training where they learn our industry, competitive advantages, the qualities of a successful sales rep, and most importantly, how to develop long-term internal and external relationships. This training is ongoing. No matter a person’s tenure, our sales department is held accountable to continuously learn. 

For our scripts and key messaging, we use typical applications such as Microsoft Word and PowerPoint. But our sales teams live in our proprietary technology platform, Accelerate. This platform houses all the data our sales teams need to make decisions on how to best serve our partners as well as when they need to engage other departments for support. 


"Some of our best company programs started as an idea that a sales rep piloted.”


What processes do you have for keeping your playbook up to date? 

We established various channels of feedback, not only for our sales teams but also for carriers and customers. These feedback channels are crucial for us to understand how we are servicing our partners. But they also ensure sales has the tools and messaging they need to be successful. The sales leadership team looks for trends in this feedback. When we see a pattern — maybe a gap in behavior or an opportunity for improvement — that is when we will make improvements to our learning and development program.

When we make a change, we try to get feedback from sales reps. If we make a change without bringing the team along, they won’t be bought into the process. Also, we know that we shouldn’t make changes all the time. Strategies need time to play out before changing them. So we are thoughtful when we update our sales approach and training, and always start with feedback. 


How do you include your salespeople in the process of developing your playbook?

We believe in piloting strategies. Some of our best company programs started as an idea that a sales rep piloted. And we ask for feedback at every level within the company, from the new hire that started two days ago to our founders.

In the last several years, we received feedback from all of our stakeholders on the importance of visibility into the status of loads. Arrive invested heavily in that technology and doing so tied into our sales approach. We evolved our messaging and scripts to over-communicate with customers and lead with our visibility capabilities.



Doug Williams, Senior Director of Sales Enablement

Doug Williams

Senior Director of Sales Enablement Doug Williams said anyone can influence the sales playbook at database company MongoDB. Being a new employee or someone outside sales doesn’t prevent an individual from contributing to the sales team’s strategy.


How do you format and deliver your sales playbook to the team, and why? 

There is no single playbook in the traditional sense. Instead, we ensure that our sellers are trained via a variety of modalities and with the support of different teams. Within a seller’s first six months, they will have participated in two week-long training events as well as one-on-one training from their direct manager, a solutions architect, the sales enablement team and others. We also bring the process to life through learning and document management, as well as call review technologies.

Continued practice is a key priority. Ensuring our sellers take the time to understand customers’ situations and apply our sales principles enables them to deliver the most value to clients.


"Continued practice is a key priority.”


What processes do you have for keeping your playbook up to date? 

Stakeholders with suggestions to improve how we sell could come from anywhere in MongoDB. There is no premium put on someone’s title. If there is a good idea that will drive greater efficiency in our process and greater value for our customers, we implement it. 

We are constantly adapting to changing market forces, new products, technologies and unforeseen circumstances. Working from home recently has forced us to rethink many processes. More responsibility is now placed on each seller’s shoulder in terms of accountability and daily discipline. And we’ve had to ensure the materials and processes we use to support them are reflective of this new reality.


How do you include your salespeople in the process of developing your playbook?

Many of our most useful sales tools come from sellers’ ideas. For example, we recently created a new discovery tool that offers quick snippets of technologies, their benefits to the customer, the alternative the customer may be using today and how MongoDB would differentiate its offerings. No one asked a seller to build it: the tool’s development was organic. A rep saw a need, figured out a way they could help, built it, asked for feedback, and it was in front of other reps in a week. It represented great initiative on the part of the seller, as well as the collaborative nature of the team itself. 


Up NextSales Prospecting: The Strategies That Can Make — or Break — It

Great Companies Need Great People. That's Where We Come In.

Recruit With Us