Scale Your Team Like a Bay Area Sales Leader

Four local movers and shakers from the tech community shared their best tips for growing a sales team — and what they look for when hiring new reps.
Written by Adrienne Teeley
January 13, 2022Updated: January 13, 2022

After a flurry of last-minute deals and ramped-up efforts to crush their quotas in Q4, January often brings with it a sense of calm for sales reps. While there are plenty of new goals to hit and fresh leads to follow, the new year offers a chance to reflect on what’s worked and what could be tweaked moving forward. 

After the turbulence of the last two years, 2022 is perhaps an ideal time to think critically about how a team’s processes have held up in a pressure-cooker environment, especially those around hiring strategies, enablement and forming cohesive cultures — both inside and out of the office. While the tech industry settles into a new normal of hybrid models, explosive growth and an ever-developing landscape, sales teams should be proactive in making sure they’re ready for whatever the new year has in store for them.

That being said, some teams have found their groove in spite of the ups and downs. Built In SF spoke to four local sales leaders who have grown their teams over the last year with a steady hand, and have succeeded in equipping their reps with everything they need to effectively sell, level up in their careers and help their peers do the same. 

 

 

Anne Karrigan
Head of Account Management

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

My blueprint for building a successful team starts with hiring the right people, onboarding them successfully and then supporting and cultivating them as sales professionals. 

Hiring is the cornerstone for success. The phrase “slow to hire” is my mantra. I’m keenly aware of how competitive the talent market is, but I wait until we find the right candidate and then move quickly. It is critical to not compromise in order to fill headcount, as you’ll waste more time in the long run.

Freshworks has a great onboarding process that provides the basics of product and pitch training that we supplement with peer mentors. Welcoming new employees is important, and I always want them to feel like they belong and are part of the team. I spend more time with employees during this phase until they feel comfortable and acclimated to getting out to market.  

After the training wheels are off so to speak, it’s important for me to be engaged as a manager and support them in the way they thrive. I always make it clear that this is a safe environment and I’d rather see mistakes from effort than perfection by playing it safe.  

 

Whats the most important characteristic you look for in a salesperson, and why?

Self-drive. Hearing “no” and receiving objections is a daily occurrence, so it’s critical to hire someone who knows how to pick themselves up after rejection, persevere and focus on the right future opportunities.  I also want to know the “why” behind their drive: What is it that gets them excited to do sales? What are their life’s goals? What are they doing all of this for? That helps me understand what is motivating them, and if Freshworks is a place where they can realistically achieve their goals, or even get them one step closer. Freshworks provides generous incentives and positive encouragement, but if the salesperson doesn’t have their own self-motivation or drive, they won’t fulfill their potential.

I also closely watch how the candidate manages the interview process. You are the product in an interview, so I observe how a candidate sells themself, follows up, handles objections and how they try to close. Sometimes our hiring decision can come down to whether they sent a thank you email. Although they may have said all of the right things in the interview, action and small details matter.  The interview process is no different than a sales process.  

 

It is critical to not compromise in order to fill headcount, as you’ll waste more time in the long run.”

 

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

Sales fundamentals and execution are integral to a rep’s success. Outreach, developing relationships, exemplary pitches, client consultation and follow-up are the basics for success. No way around it.

Measure the metrics that drive performance. Trust by default, and always have a pulse on each rep’s activity and pipeline. It’s important to set the expectations of activity early in their tenure, inspect what you expect and have accountability. 

Be involved and available. It’s important in a remote environment that my team has access to what they need, particularly for newer employees who are learning to navigate the organization. My door is always open and I stay involved in deals of magnitude.  

Team culture is important to me, and I look for complementary diversity. I want a team that is optimistic, collaborative and supportive. We have shared core values of integrity and respect. We share our wins, losses and lessons. Everyone has their own sales style and personality. I’m not trying to change who they are — I want to create an environment that sharpens their sales skills, develops their own unique sales brand and allows them to flourish.

 

 

 

Marcello Gallo
Chief Revenue Officer

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

Here’s the truth: customers don’t care that your product is the most complicated and sophisticated under the hood. Customers will only buy your product if they believe it’s the best way to achieve their goals.

That’s why a successful sales team starts with a proven customer engagement model, which demonstrates value through the lens of the customer’s goals. Get the model right and you’ll close seven-figure deals with the largest companies on the planet, as we have at Moveworks. Sure, it helps to have the most advanced product in our industry, but the science of sales is really about focusing on value for customers and helping them reach their desired future state.

My priority is to support every rep in mastering that science, so they can earn their PhD in enterprise sales. Early on, we provide new reps with guidance on managing their account list and researching their prospective customers, ensuring that we focus on their primary initiatives. It’s part of a powerful, repeatable playbook that fuels our triple-digit year-over-year growth at Moveworks — a playbook that we improve and optimize as we continue to innovate and release great products.

 

A successful sales team starts with a proven customer engagement model, which demonstrates value through the lens of the customer’s goals.”

 

Whats the most important characteristic you look for in a salesperson, and why?

Hiring the right sales reps and sales leaders is the most important fundamental. Our hiring profile focuses on three core qualities: intelligence, persistence and desire. These traits are essential to understanding our technology and sales process, and relentlessly proving its value. From there, we evaluate intangibles like integrity, coachability and intuition.

 

What other skills do Moveworks reps need?

  • Reps need to demonstrate the skills to follow a repeatable sales process, ask great discovery questions and build a powerful value statement; 
  • They need knowledge of the organizations, departments and personas we’d like to become our customers. This allows reps to use a value-based selling approach that ties customer value to a business case.
  • The experience to sell an unbudgeted SaaS product, with a track record of consistent performance using a defined sales process.
  • Finally, all of these qualifications must be balanced with a diversity of backgrounds and perspectives, which ensures a mindset of continuous improvement.

 

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

There’s no one secret to scaling a successful team. It takes deliberate planning and attention across the entire employee life cycle.

It all starts with hiring the right people, since your people define your company more than policies. Being extremely consistent with your hiring profile helps maintain a consistent culture.  

From there, you need a comprehensive approach to onboarding so reps fully understand your product, your technology and your customer engagement model. Moveworks invests heavily in sales onboarding and training, from remote “pre-boarding” courses that cover the basics to an in-person sales bootcamp that dives deeper while reinforcing our culture.

One of the most underrated factors in scaling a successful team is building relationships. Our reps regularly meet with leaders from our product, engineering, marketing, operations, finance, and executive teams, which helps us avoid silos. As a customer-centric company, every department is focused on the same goal: providing value to customers. To stay consistent while we scale, we need to stay laser-focused on that big goal.

 

 

 

Drew Sherwood
Head of Corporate Sales

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

While there are dozens of methodologies out there, any successful sales organization that consistently creates revenue and forecasts accurately must follow a standard process. 

Here at Grammarly, we use MEDDIC (metrics, economic buyer, decision criteria, decision process, identify pain and champion). The first ‘M’ stands for the metrics that the buyer cares about. Grammarly has a very horizontal application, so understanding each use case and how we can measure value throughout the process is important to help customers understand our impact. 

A cold-to-close sales opportunity is like a complex assembly line. If you miss parts of it as you go, the end result will be variable. Ensuring that you have all the parts of your sales process clearly defined with measurable goals is a crucial step in the ability to deliver predictable outcomes and demonstrate value to the buyer.  

Our team is empathetic and realistic, and we understand it’s important to evolve your process with the market. How your buyers buy and what they find important today will be different three quarters from now. Adapting your conversations to focus on how you provide value is key in making the team success.

 

Whats the most important characteristic you look for in a salesperson, and why?

Preparation and curiosity! Does the salesperson ask questions that make you stop and think, or do they ask questions that they found on a list, or have answers they could have gotten off of your website? 

Executives don’t take meetings to learn about product features. They want insights. Curious reps establish credibility early on, earning the right to ask more difficult questions without seeming pushy. Asking second- and third-level questions based on research and industry knowledge accelerates the relationship between buyer and seller, which is particularly valuable in this virtual environment. 

 

Our team is empathetic and realistic, and we understand it’s important to evolve your process with the market.”

 

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

As a mentor once told me, “Sales is not complicated, but that doesn’t mean it’s easy.” As a leader, it’s important to be trusted, vulnerable and not ask your people to do something that you wouldn’t do yourself. At Grammarly, we rigorously hire against and anchor in our values, so when someone joins the organization, we have a shared ethos, which contributes to our ability to scale. 

Every new employee has foundational training on who Grammarly is as a company and our operating principles. For the Grammarly business team in particular, since we are a newer product offering and team, we are consistently iterating our onboarding and enablement process to ensure the newest information is available to our hires. 

We are highly collaborative, and partner closely with product, product marketing and our pre-and post-sales teams. This partnership is key in getting our new hires set up for success and ensuring we are staying abreast of the competitive landscape. 

We also believe it’s incredibly important that managers coach individuals on their specific areas of skill development. We all bring something to the table, albeit in different ways! 

 

 

 

Jay McGrath
Chief Revenue Officer

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

I like to find people who are naturally curious and enjoy helping customers find solutions to their business challenges. We are very focused on building use cases that deliver value for our customers and helping them build a business case for adding Tonkean to their software toolset. Our entire sales process is built around a strong business case, return on investment and proof of value to the customer.

 

Whats the most important characteristic you look for in a salesperson, and why?

People who are willing to do their homework and to be prepared for each interaction with our customers; those who are naturally curious and good at asking open-ended questions; and people who genuinely want customers to be successful in solving their major business challenges. These attributes enable a salesperson to be successful in selling Tonkean and building solid, long-term customer relationships.

 

I like to find people who are naturally curious and enjoy helping customers find solutions to their business challenges.”

 

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

We have a four-week onboarding process that helps new salespeople learn about our product, our differentiators, and our go-to-market tools and strategies. More importantly, we learn about each team member’s preferences, motivators and what drives them to sell. We provide individual coaching and development to each salesperson, and provide them with a peer network that looks to collaborate and help. It is very much a team selling environment.

 

 

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