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A strong, high-performance sales team is critical to a successful business. But what makes a sales team truly great, and what strategies can leaders use to create a team that's highly successful? To address these questions, we're talking to CROs and sales executives about "How To Turn a Good Sales Team into a Great One." As a part of this series, I had the pleasure of interviewing Ryan Mack.

Ryan Mack

Sales standout Ryan Mack has used his 20+ years of sales, marketing and product experience and started Peer Sales Agency to help small- and medium-sized businesses close more sales too. His vision was to build a multidisciplinary, highly motivated team of salespeople, marketers, advertisers, writers, and designers wholly focused on helping SMBs grow their revenue. And what he created over the last few years is not your typical marketing agency. Peer is actually a sales agency that uses marketing to help their clients close more deals by applying their proven model that helps drive awareness, engage prospects, and convert them into paying customers. To Ryan and his team, the sales process is magical and it’s the driving force behind everything they do.

Thank you for doing this with us! To start, can you tell a bit about your 'backstory' and what brought you to this career path?

My career started in account management, helping clients implement solutions more efficiently. I quickly learned how my role as their account manager created a relationship based on trust and results. They knew how my success was directly related to their success, so we had a mutually beneficial ongoing engagement.

This role led me to sales. I didn’t want to be the sales person who curated a superficial relationship, sold the product, and then vanished. Taking what I learned from account management, I knew the most effective way to grow my territory was to provide prospective clients with value-added materials throughout their buyer’s journey. This ensured a “help-first” approach, as opposed to looking for a good commission check.

With the success I experienced in sales, it was my goal to help all the salespeople in my company by supporting them with the best sales enablement materials available. This resulted in me starting and leading our first marketing department. As the Director of Marketing, I partnered closely with the sales organization to produce content and collateral to support prospects at the top, middle, and bottom of the funnel. This resulted in a significant increase in conversions across all stages of the pipeline and the onboarding of more engaged and excited clients.

My next stop was to lead the entire product and marketing organization (50+ people). I needed to continue the impact we had in marketing, but also take a more proactive approach to product-market fit and help our engineers build solutions that our market needed. By moving into product, I was able to implement an open flywheel of communication between product, marketing and sales. With all departments rowing in the same direction, we were able to help each other develop, market, and sell the best products to the most engaged buyers.

This model of alignment led me to private equity. I implemented a powerful marketing and sales process for companies looking to grow. Each company adopted the curriculum to penetrate its markets more effectively. This curriculum also normalized the reporting of each portfolio company’s lead generation, nurturing, and closing activities, so the holding company could evaluate progress apples to apples.

As we all know, buying and selling companies is a long process. This prevented me from reaching more small- and medium-sized businesses who needed our curriculum. With that mission in mind, we exited the PE firm and started Peer Sales Agency. Our goal was simple: help SMB owners/operators find and close more deals. We know how to compete against larger competitors, and our curriculum helps businesses achieve success on an SMB budget.

Can you share an interesting or amusing story that has occurred to you in your career so far? What was the lesson or takeaway?

Let me start with the lesson—never underestimate the power of an influencer. Back in the early 2010s, I was selling a voting system to the State of Utah. These types of enterprise sales are years in the making, so it takes a lot of relationship building to have a shot at the deal. Each county was included in the procurement process and it was my job to convince all 29 counties that my company’s system was the best.

After months of work and negotiation, I had effectively won over 28 of the 29 counties – everyone except for Salt Lake. This county was the population center of Utah and wielded more influence. While I continued to work on Salt Lake County, I took the approach of everyone’s opinion mattered. Well, that wasn’t exactly true. Meanwhile, my largest competitor focused her time on the largest county. This turned out to be the right strategy and I lost the deal.

As I reflected on what happened, it became clear that one detractor out of 29 can tip the balance away from your favor. Since then, I always come into every deal making sure I understand the dynamics of every decision-maker, influencer, and champion to prevent a mistake like Salt Lake County from happening again.

Are you working on any exciting new projects now? Tell us about it!

Yes, we have developed a new curriculum (Peer Select) to support companies targeting high-net-worth individuals (HNWIs). This includes law firms, accounting firms, wealth management advisors and RIAs, bankers, and consultants. These HNWIs have a different buying strategy and tend to make purchases from folks with whom they have a relationship. Understanding this persona allowed us to create more strategies and tactics around building meaningful relationships with Centers of Influence (COIs).

Conversion percentages are very low if you’re cold-calling or expecting them to enter a digital funnel. If you want access to these people, you need a referral from one of their trusted advisors. We help our clients’ sales teams develop deeper relationships with the COIs and encourage more referral-based business.

None of us can achieve success without some help along the way. Is there a particular person you're grateful for?

I am grateful for the support and encouragement I receive from my wife. She has helped me become a more empathetic salesperson and owner. While she always retains the seat of “Top Fan”, I get the most out of her constructive feedback and unique perspective. She's more aligned with the buyer persona I am targeting, so her reactions to pitches, materials, tone of voice, and approach are invaluable to me as a salesperson.

The highest compliment she has paid me was the unwavering support to leave the private equity firm and start Peer. We bootstrapped the investment and did it on our own—no guarantees and all the risk. Because she believed, I believed. Almost five years later and we’ve doubled our revenue every year. I couldn’t have done it without her.

Can you tell us a bit about your experience leading sales teams? How many years of experience do you have, and what size teams?

I have over 15 years of experience leading sales teams, including several multimillion-dollar departments. The size of teams I have worked with ranges from four to 32, and most of my career has been spent in B2B companies selling +$200,000/year products.

The teams I have managed also vary in structure; inside sales, outside sales, account executives (up-sell / cross-sell), and sales engineers. Each plays a critical role in the revenue generation process and I cannot place more value on any one role.

What do you think makes a sales team great? What strengths or characteristics do you try to cultivate?

The best sales teams are made up of talented, goal-oriented individuals who believe in the company’s mission. They’re willing to go beyond what’s expected and deliver exceptional results.

When it comes to sales performance, great teams share both strategic and tactical perspectives. Their strategic perspective comes from having a clear understanding of their business strategies, priorities, and goals—and how all these tie into how they reach their targeted customers. And their tactical perspective comes from understanding how all the tools around them work together effectively. This includes software and sales enablement, as well as the upstream and downstream departments that help them achieve success.

A sales team is successful when it has the right combination of people, processes, and tools. When you have these three things together, they create an environment that helps your sales team thrive.

As with any department, sales can have a lot of different strengths, weaknesses, and personalities. How do you manage such diversity on an individual basis? Is there such a thing as a blanket motivator?

I believe this starts in the hiring process. One of the key responsibilities of a sales manager is to identify and hire based on which characteristics will put the rep in the best position to succeed, both internally and with prospective clients.

Depending on what you are selling and who is buying, you will weigh certain styles differently in the evaluation process. For example, you may put more emphasis on a competitive personality who enjoys winning. On the other hand, you may not place a lot of value on technical skills, as those can be taught. Evaluate which skills are critical to success in your industry, but are more difficult to teach. Those become your non-negotiables during an interview. Then develop training opportunities to shore up some of the skills that can be taught, e.g., CRM, email correspondence best practices, effective cadences, calling scripts, etc.

Finally, establish departmental KPIs with salesperson-specific quotas to help remove the subjectivity and ambiguity around managing sales talent. Their scorecard becomes the blanket motivator and stays with them every day.

What strategies have you tried to increase motivation, engagement, and productivity? We want to hear it all—the stranger, the better!

I have tried many different strategies to get more from the sales team, and how they can get more from the organization. Here are some examples:

  • Ride-alongs – I believe wholeheartedly that walking a mile in someone else’s shoes can provide you with a perspective that you normally would not have.
    • Spend a week with a Product Manager to see how they evaluate the market and make recommendations to Development.
    • Partner with a representative from Marketing to help them understand what is most helpful for winning deals.
    • Help Account Management with onboarding a new client to see where there is a potential disconnect between what you sold and what is being delivered.
  • Competitions – While there is always competition for rainmaker (top salesperson), this is more self-serving and doesn’t necessarily bring the team closer together. Instead, I like to challenge one salesperson with a short-term goal (one week to one month), and if they achieve the goal, the whole team is rewarded. Not only does the salesperson feel some pressure to succeed, but the team develops a help-first mentality and they all work together to achieve the goal. It’s great for team building.

Of all the strategies you’ve tried, which did you find to be most effective? How did this have a direct correlation to sales?

The ride-alongs are by far the most impactful strategy I have implemented. What starts as siloed departments unwilling to help each other, evolves into an open communication flywheel where ideas and feedback flow back and forth between departments. You now have many minds working together on a common goal, versus disparate departments assuming they know what’s best for the others.

The results are massive:

  • Ideal customer profile is more targeted and specific to boost qualified prospects
  • Buyer personas are more detailed to ensure a smoother sales process
  • Product-market fit is stronger and helps excite the market for your offering
  • Messaging better differentiates you from your competitors
  • Onboarding is smoother and results in less churn
  • Sales cycle is faster and results in more engaged clients
  • Average price-per-sale increases because you’re better at selling value

Can you tell us about a time that your sales team outperformed their targets? How high over did they go, and what was that like for everyone?

Every year we would set our revenue targets at 120% of the previous year. This was a standard practice set by the revenue organization and was validated by YoY performance metrics.

The first year we implemented the ride-alongs, we achieved 190% of our goal, more than doubling from the previous year. We spent more time as a collective team (product, marketing, sales, and account management) to produce better product features, messaging, processes, and implementations. We established common metrics between the departments to promote alignment. The sales team won big that year, but instead of hoarding the commissions, they pooled some of the winnings and purchased gifts for their non-commissioned teammates. These included iPads, Apple Watches, group dinners and gifted PTO. The culture completely changed that year and it was all because people were thinking about each other and not just themselves.

Great things often take time. What do you think is a realistic timeline to take a sales team from good to great?

I believe this transformation can be realized in as little as 12 months.

Based on your experience and success, what are the five strategies that will help turn a good sales team into a great one?

  1. Evaluate your current team against the core values from which you hire and fire sales talent. For those folks missing the “non-negotiables”, you need to transition them out of sales and find their replacements.
  2. Recruit new sales talent against these same principles and immediately see an uptick in overall team performance.
  3. Define, develop and implement the proper tools and processes for the team to do their jobs. Switching your CRM software, enrolling in sales or product training, developing more effective sales enablement materials, etc. You can’t effectively or efficiently hammer a nail with a screwdriver.
  4. Create a collaborative environment for cross-departmental support. Understanding the role every team member plays will help you identify, discuss and resolve issues plaguing the growth initiatives.
  5. Develop departmental and individual scorecards that are aligned with the company’s key business objectives. Report on these scores weekly and provide merit increases based on performance.

Lastly, if you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be?

Without a doubt, I would find a way to pull impoverished people out of that cycle and give them access to sales and marketing jobs. Very few people are taught sales in high school or college, which means we all learned how to do it later in life and on the job. So, that means I don’t need your experience as much as I need your will and desire. 

How can our readers further follow your work online?

Great question, you can follow me and my company at the links below.

Personal LinkedIn: https://www.linkedin.com/in/ryanmack/ 
Company LinkedIn: https://www.linkedin.com/company/peer-sales
Website: https://peersalesagency.com/ 
Blog: https://resources.peersalesagency.com/tag/article
Podcast: https://resources.peersalesagency.com/tag/podcast 
Facebook: https://www.facebook.com/peersalesagency/ 
Instagram: https://www.instagram.com/peersalesagency/
Twitter: https://twitter.com/peersalesagency 

By Phil Gray

Philip Gray is the COO of Black and White Zebra and Founding Editor of The RevOps Team. A business renaissance man with his hands in many departmental pies, he is an advocate of centralized data management, holistic planning, and process automation. It's this love for data and all things revenue operations landed him the role as resident big brain for The RevOps Team.

With 10+ years of experience in leadership and operations in industries that include biotechnology, healthcare, logistics, and SaaS, he applies a considerable broad scope of experience in business that lets him see the big picture. An unapologetic buzzword apologist, you can often find him double clicking, drilling down, and unpacking all the things.