Solving the Siren Song of Scalability

Sometimes you have to look back to move forward when growing your company.

Written by Jeff Kirshman
Published on Jan. 11, 2022
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Your company is growing. Demand is increasing. The siren song of scaling wails in the distance. 

These are the realities of a thriving business, and they don’t leave much room for reflection. Growing a sales team, in particular, requires new systems, strategies and infrastructure — a process that favors decisive action.  

Still, it’s imperative that you resist the allure of immediate expansion at the expense of your long-term goals. Sustainable growth calls for patience and intentionality. As exciting as the future may be, it is not an invitation to abandon the methods that brought you here. 

“As we continue to scale, it’s vital to not lose sight of where we started in the midst of where we are going, and that goes back to the collective team,” said Brissia Perez, senior sales manager at fintech company Melio

Scaling passion and belief, in other words, is just as vital to a company’s success as retooling your revenue forecasting. That’s why Built In NYC checked in with five local tech professionals to learn how they weather the storm of expansion when assembling a fleet of sales team operatives.

 

Image of Brissia Perez
Brissia Perez
Senior Sales Manager • Melio

 

What’s your blueprint for building a successful sales team? 

Team camaraderie is huge. As a manager at Melio, leading with empathy builds trust and develops a community in which reps want to show up and succeed each day — not because they have to, but because they believe in the group they’re a part of. Sales is a field that takes grit and hustle, and keeping my team motivated and encouraged is integral to my role as a leader. Fostering a collaborative, transparent and fun working environment helps to build and scale successful teams from the ground up.

Leading with empathy builds trust and develops a community in which reps want to show up and succeed.”

 

What’s the most important characteristic you look for in a salesperson?

Coachability and positivity are important characteristics. Experience is gained throughout your career. However, having a great attitude and being eager to learn is something that is ingrained in an epic salesperson. It’s also vital to be willing to give and receive feedback. A person who welcomes feedback is always looking for ways to improve themselves and their team.

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

Part of the beauty of startup culture is working collaboratively with your peers. Regardless of level, there is always the collective “we” within a team that I lead. I literally could not have built and scaled-out this division without the passion, hard work, energy and effort of each rep along the way. As a leader, I’m here to give and receive feedback, as well as provide my reps with the tools and support they need to be successful. What makes the team so special is that we have built the culture to feel like a win as a team, rather than a win as an individual.

 

 

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Russ Malz
VP of Worldwide Sales • Hyperscience

 

What’s your blueprint for building a successful sales team? 

Over the past five years, I’ve been fortunate to manage teams that are growing up to 100 percent per year. Because salespeople want stability, and high growth requires change by definition, there’s a very important balance a sales team must strike to have sustainable long-term success. It’s a dynamic process. Three key elements of my blueprint for building a successful sales team at Hyperscience include communication and transparency, sales leadership empowerment and taking a macro view each quarter.

First, it’s essential to set a clear goal, communicate the goal and share where the team is against that goal. The second aspect is empowering sales leadership — and especially first-line leadership. That’s a key ingredient to helping companies respond to market dynamics quickly. Finally, it’s important to look down the road and not get stuck in a rut focusing too much on hitting quarterly numbers. If you are growing by 100 percent year over year, incremental changes should be made on a quarterly basis. Then, at the end of each quarter, evaluate and adjust the plan accordingly.

It’s essential to set a clear goal, communicate the goal and share where the team is against that goal.”

 

What’s the most important characteristic you look for in a salesperson?

I call it “learnability.” This is a combination of a willingness to learn new things continually, an ability to adapt to change, and being coachable and open to input not only from management, but also from different parts of the business. The world is changing very quickly; technology is changing, new software and service offerings are being rolled out daily, and old models get stale quickly. By being hyper-aware of emerging trends and business models, salespeople with high learnability are having the most success.

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

This is perhaps the most challenging aspect of scaling a team, particularly when a company is in hypergrowth mode. There is no silver bullet, and one additional challenge is that the rate of change of software development is increasing quickly — and the result is that training gets old very fast. Some of the best practices I’ve seen recently to train and hire while maintaining culture include interviewing with at least three people and several organizations, since having a broad view of a candidate can avoid costly hiring mistakes. Secondly, get new hires busy and engaged as quickly as possible. One effective way to do this is to pair new hires with a successful sales rep and have them participate early. Another way to do this is to have new reps pursue small deals to get more at-bats. Finally, for training, keep it modular, quick and fresh. That way, similar to agile software development, training for today’s sales reps never becomes antiquated.

 

 

Image of Cheri Barber
Cheri Barber
Senior Sales Manager, Enterprise • Rhino

 

What’s your blueprint for building a successful sales team? 

Building a successful sales team begins with great products and an encouraging culture, and Rhino certainly has both. Two attributes that fuel our success are passion for the product and company mission, and consistent collaboration and communication.

Every person on our team truly believes that Rhino’s deposit insurance is changing the housing affordability crisis for millions of Americans. Everyone on the team has a story about how they have been affected by security deposits. One teammate went to NYU. One semester, he and his family had to come up with $15,000 for his first month’s rent, a security deposit and a broker’s fee. With these personalized experiences, it allows the team to be more empathetic to both the resident and the property management company or owner.

Especially in our virtual world, it is vital to stay connected to each other to share wins, challenges and new ideas. In addition to team meetings and weekly one-on-ones, we all talk, Zoom and utilize Slack every day for updates, pre-meeting preparation and to celebrate progress on deals. We also have frequent training sessions, panels of experts and roundtable discussions to continue sharpening our skills and knowledge.

Especially in our virtual world, it is vital to stay connected to each other to share wins, challenges and new ideas.”

 

What’s the most important characteristic you look for in a salesperson?

Critical thinking encompasses all key elements needed to attack the sales cycle. In order to even connect with a prospect, you need to utilize different personalized methods of communication to get their attention. So many people are vying for your prospect’s attention. Quickly identifying what is and is not working and making immediate changes is crucial to initial success.

Once you have your prospect’s attention, thoughtful questioning and problem solving come into play. In an effort to respect your prospect’s time, pre-meeting preparation is essential. This will help drive an engaging and productive dialogue to move the conversation forward. It is common to face unexpected objections, but the critical thinker does everything they can to anticipate objections and address issues should the unexpected arise. 

Critical thinkers have a teaching and coaching mentality. They work with customers as a collaborator instead of pitching ideas to see what fits. They understand that it is more than a sale — it is a relationship that leads to new opportunities for growth for both parties. They are more interested in helping than getting credit.

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

Each teammate brings their own personality to the table, which makes sales so fun, but knowing where the gaps are on the team builds cohesion as the business matures. Having members of the team committed to the mission and culture continues to impact the growth of the company. Being able to maintain the energy that contributes to expansion, and having the wherewithal to include new perspectives for growth, positions teams for success. 

Maintaining an open-minded approach while valuing processes that have brought wins and repeating that with consistency allows customers to rely on the ambitious standards they have come to expect from the business partnership. Each member of the team is able to truly bring their own talent and flavor to the mix, and that talent is honed and sculpted through mentorship, coaching and development. When an individual is being considered for a new position, they are interviewed at multiple levels and by multiple members of the team so that we can bring them into the fold. That way, they are already connected to current team members and get to see the culture in action.

 

 

Image of Jonathan Pollack
Jonathan Pollack
VP of Revenue • Augury

 

What’s your blueprint for building a successful sales team? 

There are three pillars that are crucial in building a successful sales team at Augury: people, process and tools. Getting the right people into the right roles makes everything easier and offers the ability to transform your business. Change is constant and communication is increasingly difficult across the organization as companies scale rapidly. When you have the right people with the skills to drive the business forward, they will be able to operate in an environment of imperfect information. 

Great care and diligence should be put into the recruiting process to ensure we’re making the right hires. Defining scalable processes is also important in building a successful sales team. In most cases, we can look at a process and multiply it by the number that we expect it to scale to and inherently know if the process will break. More important than the specifics that we are defining are the incentives behind it. In order to drive the behaviors that the business needs, refer to the compensation plan. Outfitting your people with the best tools is the last step in supporting a successful sales organization. It should only be done once the right people and process are in place.

 

What’s the most important characteristic you look for in a salesperson?

The best salespeople are honest, smart, hardworking and persistent. They push the envelope, hustle and are great communicators and listeners. The reason we look for these traits is that they cannot be taught. They are innate.

Good management knows how to build processes, and great management knows when to break processes.”

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

This question really comes down to how an organization balances innovation and an adherence to repeatable and scalable processes. To put it simply, good management knows how to build processes, and great management knows when to break processes. All in all, I think it comes down to aligning the team on the “whys” behind the business. Creating clarity about why certain decisions are made helps people understand where they can apply creativity and innovation. Repetition is key here. Many times we think that senior management’s perspectives are well known, but often they are not.

 

 

Image of John Carson
John Carson
Chief Revenue Officer • Ideon

 

What’s your blueprint for building a successful sales team? 

The culture I shoot for at Vericred resembles my approach to golf: You always want to play with the best so you can learn from the best. 

 

What’s the most important characteristic you look for in a salesperson?

It’s hard to choose just one. I always prioritize ethics, energy and self-motivation. I was told years ago that you don’t motivate people — you hire motivated people and simply remind them of what motivates them.

You don’t motivate people — you hire motivated people and simply remind them of what motivates them.”

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place?

In order to build a strong team, you need repeatable processes and procedures. I strongly believe it’s important to make the team a part of that building process. Leverage your team’s knowledge, and they will be evangelists among their peers and new hires. As they say, people support what they help to create.

 

 

Responses have been edited for length and clarity. Images via listed companies and Shutterstock.