For the better part of my 18 years at Salesforce, and throughout my nearly two years at Procore, I’ve been on the front end of scaling PreSales teams during periods of rapid corporate expansion.

Steering PreSales teams through hyper-growth phases has been an exhilarating, adrenaline-charged experience. It would be an understatement to say it’s been rewarding.

Of course, scaling teams isn’t always easy, and I’ve faced many challenges along the way. Unfortunately, there is no magic formula that PreSales leaders can use to guarantee success in navigating uncharted territory. There are, however, a few things I’ve learned in my career when it comes to scaling PreSales teams that you may find helpful.

Successfully scaling PreSales teams requires effective people-management and process-management in equal measure. What it comes down to is a steadfast commitment to maintaining your organizational culture and a rock-solid plan in place for implementing your process.

Scaling PreSales with Culture

Establishing a robust organizational culture is critical to growing a company that endures the test of time. In my early days at Salesforce, and later Procore, I’ve learned that creating and sustaining an organizational culture is a bit like the experience of being a parent: when you have your first child, you have no clue what’s going on. With your second, you understand the process, but what remains elusive is the personality that they will develop over time.

The same thing is true as a company begins to grow. In the case of Salesforce, that growth was incredibly rapid.

How do you establish and maintain an organizational culture during periods of rapid growth?

Salesforce evolved very quickly from the point where you knew everyone in the building to the point where introductions to new managers and colleagues came at a dizzying pace.

One of the things that Salesforce did incredibly well was that they named their culture. “Aloha” became the culture’s brand and vibe. When we onboarded people, “Aloha” was an integral part of the experience, and each person became responsible for upholding that culture. We embraced it – and everyone who joined the organization did, too.

We were also shifting teams around quite a bit – at times, the converging teams were focused on wildly different objectives – but as these shifts took place, we were able to instill a strong sense of culture along the way. In some ways, our shared culture was the only baseline that we had.

While the official name and internal branding have evolved over time, the essence of Salesforce’s culture is still very much alive today, and it is articulated and manifested throughout every aspect of the organization.

Prioritizing Organizational Culture and Workplace Engagement

When I joined Procore in 2019, I recognized some similarities with Salesforce in terms of how it prioritizes its organizational culture and workplace engagement. Like a lot of companies, we don't have a formal name for our culture, but we still live it through our values: openness, ownership and optimism.

Our values are our foundation, and we work to create and maintain a culture where each of us has a sense of ownership of our work, and we’re encouraged to try new ideas – all while in an open, collaborative environment.

Put simply, organizational culture is the lifeblood of a company.

I’ll never forget the cautionary tales shared with me by leaders at some of the top Fortune-500 companies about the importance of organizational culture and the role it played in determining their success – or failure.

According to these leaders, when their companies were at the top of their game, it was due to the fact that they had invested in their organizational culture. In fact, culture was the engine driving their success. Inversely, when their companies showed signs of failing in any way, it was attributed to the loss of that culture.

It’s for this reason that culture is the very last thing I think about at night and the very first thing I think about in the morning; it’s that important.

How do you ensure your culture is “working”?

The best way to ensure your culture is working is by checking in with your people. And while you’ll automatically check in with your newest people, don’t overlook your tenured and remote people.

Listen In

When I joined Procore, the first thing I did was to set up skip-level meetings with every member of the team. What I soon discovered was the collective passion the team shared for the culture.

I spent a great deal of time listening, not only to my team members, but also to approximately 200 others.

I did this to gain an understanding of the perceptions of the team, the company, and quite honestly, to uncover issues and challenges.

Dig Deeper into Surveys

Surveys that measure employee health and culture have become ubiquitous at organizations today. Surveys serve a purpose, but what I’ve learned is that when people respond to these surveys, they don’t always answer the questions that are being asked, meaning that much the feedback is nuanced.

So, it’s critical that leaders dig a little deeper into the context survey responses to be sure we fully understand it.

It’s also important to avoid knee-jerk reactions to issues uncovered by surveys, because this can lead to solving the wrong problems. Also, leaders need to respond to what’s going well, and look for ways to do more of that, rather than becoming fixated on what needs to be fixed.

Engage an Advisory Council

One thing that’s proven beneficial to cultivating the culture at Procore is an advisory council populated by individuals from across the organization who serve as the organization’s eyes and ears. They provide amazing insight and feedback at our quarterly strategy meetings.

Procore embraces the advisory council in many ways. We give them early access to some information, and we test things like messaging to find out how it lands, where we need to go deeper, and where we need to pull back.

Scaling PreSales with Process

When it comes to scaling PreSales, and when you’re introducing new processes into your organization, being a driver of change means you must be prepared for – and know how to overcome – roadblocks. There are a million different approaches out there, but I believe that changes in process should always center on what’s best for customers and what’s best for the company.

Lead with Data

Dr. William Edwards Deming said it best: “In God we trust. All others must bring data.” When you’re trying to introduce change, you must constantly measure and you must lead with data.

Let’s face it: change can lead to some uncomfortable conversations. But when you lead with data, you eliminate a lot of the emotion from these conversations. When you talk about making a change for a customer or making a change for the company, you need to back up your argument with data.

Get Outside Perspectives

It’s all too easy to rely on your own interpretation of data. Even the most well-intended among us have the tendency to skew the numbers in order to tell the story they want to tell.

Engaging with internal partners like Strategy, Ops, or Finance – entities who don’t necessarily have a horse in the race – keeps you honest. It also provides an objective point of view and an outside perspective to validate your thinking.

Start Small

As tempting as it may be to make sweeping changes, it’s better to go for a more subtle approach. Think grassroots rather than a top-down approach to change. Top-down mandates tend to be met with resistance. Effective movements start at the fringes and work their way inward, and as they progress inward, they gain momentum.

Anticipate Failure

Just as you need to define your goals and objectives around the process, you also need to prepare for failures as you go. Kicking the can down the road wastes time and resources, so it’s imperative that you define your criteria for failure. What does failure look like?

If you hit your failure criteria, what will you do? Will you tweak, pivot, or kill your current plan? It might seem counterintuitive – and downright frightening – to plan for failure, but when you assume that some degree of failure will happen from the outset, the fear dissipates.

Maintain It

I can’t tell you the number of times that I created something I thought was amazing, only to watch it die on the vine the day it was released, simply because I didn’t have a maintenance plan in place to keep it going. The moral of the story is to nail your process before you drain resources. Don’t rely on quick fixes along the way.

Create Bubbles

Create an incubation team within your team – bubbles dedicated to iterate and innovate new ideas and solutions. Sometimes you’ll need to give bubbles so much autonomy that it’s as if you’re walling them off from the rest of the organization, but this freedom will enable them to do cool things. Just be sure you create a path for these groups.

Treat bubbles like a venture model: give them an escape velocity where they can eventually break free from the stable environment of your team and integrate into the business.

A word of caution: if you don't have a strategy plan in place for the group, be ready to face challenges.

How is the group’s strategy aligned to your overall business strategy? Really think through the good, bad, and steady-state scenarios.

As these bubbles evolve into teams of their own, make sure you’re communicating about them to key stakeholders – and that you’re doing so on the front end. The death of a small, developing team is when others ask, “what’s that group, and what do they do?”

Create excitement by issuing teasers about the group’s upcoming releases. Keep others interested in knowing what’s just about to drop, and soon they’ll be checking in for the latest on what the group is doing.

Expand Specialization

I’ve led multiple specialized functions at Salesforce including innovation program business value demo engineering, and I’m currently in the process of expanding specialization at Procore. (In just under two years, my

SE team alone has grown from 30 to 80 members.) One question I hear a lot from PreSales leaders is: “How do you know when to begin introducing specialization into a PreSales team?”

Expanding specialization in PreSales is an art and a science. There is no one-size-fits-all formula; the best approach for Company A might not work for Company B. Speaking from the standpoint of a vertical construction SaaS, here are factors to consider on the “art” side of things:

  • The depth and complexity of your products. Let’s say you’re going from a single product to a multi-product environment, or the complexity of one of your products is increasing. It’s probably time to introduce specialization.
  • Employee burnout fatigue and rework. One sign that you may need to introduce specialization is when people are spending more and more time on prep work, or redoing certain things when they're getting ready for demonstrations or discovery calls.

Now let’s drill down a bit more into the “science” side of things by focusing on the following metrics:

  • ASP
  • Deal size
  • Number of products
  • Attach rates
  • Win rates
  • Team size
  • Ramp time
  • Rep productivity

Here’s an example: if you're looking at increasing the number of products you’re offering, and you can increase our deal size, you’ll drive up your ASP; if you drive up our ASP, you’ll improve rep productivity; if you improve rep productivity, you’ll drive growth for the company.

Follow the Money

I can't emphasize this enough: it’s vital that you measure and track relevant data as you define and articulate your growth plans. In short, follow the money. Begin by defining and tracking relevant data that helps you answer the following questions:

  • Is your attach rate on certain products starting to go up?
  • Is that attach rate jumping up deal size, and is deal size jumping up rep productivity?
  • Is rep productivity driving growth?

Relevant data will empower you to build a business case for additional resources, and relevant data will help you demonstrate the value of bringing on more people. With relevant data, you’re in a better position to “sell” your plan for investing in specializations to stakeholders and partners in finance, strategy, and sales.

For example, you might say: “We will align one value consultant for every second line manager. For every 30 SEs, we’ll add one demo engineer, because we know that demo engineering is a cost resource that provides a tremendous value out of the gate.”

Armed with relevant data, you’ll be prepared to answer the inevitable question, “In what ways will scaling specialized resources, rather than tapping into generalized resources, positively impact the organization?”

Remember to share data with your team. Top-level growth metrics will help them understand how they fit into the puzzle.

When you’re seeing success in expanding specialization in PreSales, don’t be surprised when you receive a larger budget allocation. Congratulations! You’re on track for even more growth, and you can apply the knowledge and experience you’ve gained from your initial scaling efforts as you dive into the next phase of expansion.

Josh Aranoff leads Global Solution Engineering at Procore. Previously he headed up Salesforce’s applied innovation program, business value, and demo engineering programs. When he is not sparking innovation across the globe, Josh enjoys spending time with his family, building mobile apps, and participating in the Bay Area CrossFit community.

Connect with Josh on LinkedIn.

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The Leadership collective is a group designed for PreSales leaders in a management capacity (Manager+ title) who are looking to network, grow professionally, and actively participate.

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