Creating Your Own Sales Cinderella Story

Creating Your Own Sales Cinderella Story

One of the best things about March Madness is a Cinderella story. This is the team that comes out of nowhere, surprises everyone, and advances beyond anyone’s expectations. Sure, we expect perennial powerhouses like Duke and Kansas to do well. And we set our brackets accordingly.

This year, all eyes were on the Saint Peter’s Peacocks. A school of 3,000 students from Jersey City, New Jersey, they knocked Kentucky and Purdue from the Sweet 16. They then fell to North Carolina in the Elite Eight. But their run puts Saint Peter’s on the map and ensures an enduring legacy.

In sales, we can learn from a Cinderella story. Of course, we love an underdog. There’s something epic and inspiring that recalls David and Goliath. But like a college basketball team, it takes guts, grit, and teamwork. It shows it’s not the size of your organization. It’s not your blue-chip name. Though these things matter, success starts with your team members believing in themselves and each other. Here are ways to create your own sales Cinderella story:

Team-First Culture

The best basketball teams and sales organizations have positive cultures. This starts with an environment that fosters teamwork and encourages success. Whether it’s an athletic director, a coach, or the C-suite, culture starts at the top. Here are ways to build your sales team’s culture:

  • Attract and retain the right people
  • Compensate fairly
  • Emphasize achievement
  • Enable success
  • Reward hard work

In a positive culture, people are paramount. It’s not that every player or seller is the best in the game. Instead, it’s onboarding those with the right traits to support your team vision. It means valuing values over skills. Sure, skills are important, but they can be taught. They can be practiced. Within a winning culture, positive people breed positive results.

Compensation counts. Of course, there’s some debate about paying college players, but compensation is more than money. It’s treating each team member as important. It’s showing they are valued. In sales, this means a competitive salary that rewards hard work. Just as sellers add value for clients, organizations should add value for their team. This includes flexible hours, work-from-home days, and provisions for families. These things attract and keep top talent.

Success starts with a winning mindset. It’s a coach who puts players in a position to win. For sellers, it’s organizations and managers that enable salespeople with the tools, resources, and motivation to excel. Success isn’t an accident. It’s coaching with a plan. Like drawing plays that free shooters, sales managers teach, encourage, and praise sellers for their activity and achievement.

In a winning culture, managers reward hard work. For basketball payers, this means earning game time and trust. For sales organizations, it means updating comp plans, staying competitive, and providing opportunity. A good culture is never stagnant. It must change and grow. You need people who change and grow with it.

Know Your Role

On both winning teams and sales organizations, players know their roles. If your job is three and D (a three-point shooter and lockdown defender), this means taking open shots. Make or miss, if you hesitate, you hurt the team. It’s knowing a timely steal or deflection is as good as a score. For salespeople, it’s understanding your role in the organization. Here are some common positions:

Sales Development Reps: These sales reps are lead generators. Their job is prospecting and qualifying leads. It involves a lot of research and interaction to build rapport and generate interest. Their main goal is building engagement and moving prospects to opportunities.

Account Managers: Instead of prospecting, these reps manage the client and their account. This means ensuring their needs are met. It also means upselling and cross selling when appropriate. More than anything, customer satisfaction is paramount.

Account Executives: AEs are process oriented. From demonstrating products to overcoming obstacles and negotiating contracts, AEs are full service. This position experiences the highs and lows and selling. Like point guards are floor generals, AEs are bosses of individual accounts. With all that responsibility, it’s high stress and not for everyone.

Sales Operations Managers: Like a basketball coach, a sales manager’s goal is ensuring your sales process runs smoothly. Sales operations managers keep their operation simple and uniform. They require organizational and technological skills. They are half number cruncher and half motivational speaker. They understand the KPIs of sales and how to get the most from their team members.

In addition to knowing their jobs, all must understand their place in the organization. Like a basketball team, a sales team is only as strong as its weakest link. What’s the point of an “and one” opportunity if you can’t hit a free throw? Why pass if your teammate can’t make a play? In the same way, why develop products if you can’t demonstrate and differentiate? Why build rapport if you can’t keep a client happy? It’s the seamless integration of all positions that makes a winning team.


As with a basketball team, sales coaching is critical. Winning coaches not only win games; they build a culture of winning. On and off the court, they exemplify excellence. They inspire and motivate. They bring out the best in their players. Here are some essential aspects of coaching:

  • One-on-one coaching
  • Group coaching
  • Assessment
  • Teaching

One of a coach’s primary responsibility is working with individual players. Of course, all players are not equal. Some are veterans and some are new. As in basketball, sellers are not cut from the same cloth. Expectations and motivations are different. Successful sales coaches understand a rep’s psychological makeup. This helps inspire them and buy-in to the team’s larger objectives.

Further, individual coaching lets managers hon in a seller’s strengths and weaknesses. This means listening to both real-time and recorded calls. It’s offering accurate praise and pointed suggestions. It’s setting realistic expectations and targets. More, it’s guiding reps to these goals and not letting them flounder and flail.  

Team coaching is equally important. After developing reps as individuals, coaches make the parts work as one. This is as essential in basketball as in sales. As coaches call plays, players need know their role, be it running off a screen, setting a pick, acting as decoy. In sales, account managers must know what BDRs say to prospects. They should understand the expectations and the needs uncovered. In addition, group coaching sets the agenda for the quarter, including targets and goals.

Today, at both the collegiate and professional level, basketball is analytics based. Beyond the X’s and O’s, this is understanding a player’s strengths and weaknesses. It’s knowing the percentages of success and failure. It’s what makes a shot “high percentage” and allows you take the best chance.

In a similar way, sales is also analytics based. With countless KPIs, quotas, and goals, selling has become increasingly mathematical. Of course, measurement is essential to gauging performance. Reps need to know their targets for calls made, deals closed, etc. They need to know what both their manager and the organization expects.

However, beyond numbers, good coaches remember the human element. Neither basketball players nor salespeople are robots. They’re human beings, with thoughts and feelings, both spoken and unspoken. As we expect our reps to know their clients, managers must know their team members.

The best coaches are teachers. Of course, managers should provide written feedback. This maintains transparency, and it allows accurate assessment. However, beyond this, basketball players and sales reps will remember their coach on the floor.

Either on court or in a cubicle, managers should guide their team’s movement or sales calls. They should offer tips, tricks, and sage advice. They have sales stories from their own experience. They know when to be stern and when to be kind. More than achieving a score on a board or test, it’s opening and inspiring young minds. It’s motivating them to achieve beyond their expectations. 

Just as a sales career is not for everyone, not all sales reps are meant to be coaches. Remember this when evaluating your team members. Most great coaches were not great players. In the same way, all great managers were not high achieving reps. In coaching, look for an obsessive knowledge along with the people skills to guide, teach, motivate, and inspire.

Sales Training

Despite the benefits of sales coaching, it can be insular. After all, both your reps and managers are part of the same organization. While this is critical for formulating organizational goals, it can be limited in real-world application.

In addition to coaching, sales training is vital to peak performance. Outside experts can build on the skills and behaviors needed to succeed. In basketball, it’s a coach bringing in former stars. In sales, it’s partnering with a top-notch training organization. Here are some essentials for successful sales training:

  • Curriculum
  • Interactivity and engagement
  • Skill training
  • Behavior modification
  • Outside assessment
  • Reinforcement

All sales training organizations have their own curriculum. When selecting one, it is essential to know your needs. From building critical skills, such as cold calling or engagement to presenting and negotiating, training can boost performance. However, foresight is critical. Before choosing the best curriculum, you must know you team’s strengths and weaknesses.

All teachers know, successful lessons require engagement. Studies show students learn and retain more when they engage the material. In addition to curriculum, the right trainer can reach individual students. Therefore, sales trainers must be as personable as they are knowledgeable. After all, experience only matters if it can be conveyed effectively.

In addition to sales experience, inquire about technique. While some trainers are active, charming, and enthusiastic, others are more reserved. One is not necessarily preferable over the other. However, you should match the trainer to your team.

In addition, you should know the specific skills and behaviors you want to improve. Maybe your team excels at the basics but falters in the end game. In this case, select a trainer who understands presenting and negotiation.

Today, as the sales environment changes, sellers need technology more than ever. In addition to your CRM, sellers must understand automation tools. Also, as we saw with the pandemic, virtual is a vital aspect of selling. Be sure your team is up on the best practices.

Further, sales training needs proper reinforcement. Of course, part of this is coaching. And the best training partners include specialized training for your coaching initiatives. Also, most training partners feature curriculum customization along with periodic reinforcement and assessment. These can be sent directly to your reps to ensure they retain the lessons learned in training.

For fans, there is nothing like March Madness. In the frenzied pace of blowouts and upsets, it can take a minute to identify the Cinderella story. This year, it was easy. After beating Kentucky, Saint Peter’s emerged as the sentimental favorite. Despite countless busted brackets, fans cheered their follow-up victory over Perdue. Even after falling to North Carolina, everyone now knows the Peacocks.

For sales organizations, it’s similar. When meeting or exceeding quota, we immediately recognize high performance. However, like a basketball team, there’s more behind on-court achievement that makes a Cinderella story. It can be shocking, but it’s no accident. It takes hard work, dedication, and an unwavering belief in your team. With the proper sales enablement, coaching, and training, your organization can similarly overachieve. And no matter what your industry, you can punch your own ticket—in the big dance and beyond.