How to Build and Scale Enterprise Sales Teams

Key principles can guide new sales leaders to success.

"Hire the right people, build a power culture where people feel trusted, respected, and they love coming to work. And then three, lead from the front, be willing to get your hands dirty..."

- Reggie advises focusing on talent acquisition and culture building. - Leading by example inspires teams and fosters respect. - Engaged leadership drives team performance.

Rapid scaling can challenge maintaining a strong company culture.

"My challenge is hiring, hiring fast, hiring smart, maintaining the awesome sales culture that we've created."

- Reggie focuses on hiring the right people deliberately. - Building an environment where people feel trusted and supported. - Avoiding rapid, careless hiring prevents cultural dilution.

Early evaluation is key to ensuring new team members are a good fit.

"Within a few weeks... you know if you've made a hiring mistake or if someone's good."

- Reggie emphasizes the importance of a certification process. - Signs of poor craftsmanship can appear early. - Rapid feedback helps address issues or confirm fit promptly.

Certain traits from athletics translate well into sales roles.

"Discipline, work ethic, being part of a team, being coachable... all those things that make athletes successful translate well into professional sales."

- Reggie notes that discipline and teamwork are crucial in sales. - Former athletes bring competitiveness and accountability. - Resilience from sports aids in handling sales challenges.

Keeping team morale high is essential when goals are missed or challenges arise.

"I focus on inspirational leadership, making sure people always stay connected to their why, like what gets them out of bed every day."

- Reggie connects team members to their personal motivations. - He uses motivational quotes to inspire the team. - Fostering a supportive environment helps maintain morale.

Focusing on specific industries can improve messaging and customer engagement.

"We made the decision to do it [verticalize] very early because we know those are the industries where we can make the most impact..."

- Reggie believes verticalization helps understand industry trends and personas. - Speaking the client's language enhances value and relevance. - Early verticalization can accelerate growth by targeting key sectors.

Innovative pricing models can enhance customer trust and adoption.

"They no longer have to pay for the right to use software... they pay for outcomes. Did our agent solve a problem?... If so, we get paid."

- Reggie introduces outcome-based pricing to align with customer success. - This model reduces risk for customers and shows confidence in the product. - Paying for outcomes fosters long-term partnerships.

Recruiting top talent to a startup requires convincing them to take risks.

"I had to convince highly compensated, super talented people... to take a pay cut and come join our pirate ship."

- Reggie focuses on sharing the company's vision and potential impact. - He emphasizes opportunities for generational wealth if they execute well. - Highlighting mission-driven goals can attract talent despite lower initial compensation.

Adapting strategies to new environments is vital for startup success.

"When I went to Slack, what I didn't do is just take the Salesforce playbook and try to implement that at Slack. I went in and listened and learned."

- Reggie stresses the need to tailor approaches to the specific company. - Listening and learning help understand what makes the new company successful. - Implementing past strategies without adaptation can lead to failure.

Effective leadership is crucial when building a startup team.

"I came in with humility, with respect, listening, putting people first. In my career at Salesforce really flourished because I reinvented myself based on failing as a CRO with a big ego."

- Reggie emphasizes the importance of humility and listening. - Reinventing oneself after failures can lead to success. - Putting people first fosters team growth.