6 ways to align your GTM team as you move up market

Like your product, your GTM team needs to evolve to move up market. Here’s how 4 industry leaders are thinking about enterprise-readiness.

I guarantee that if you’re on a B2B GTM team, you hear the word "enterprise” in nearly every meeting. But have you ever slowed the conversation down enough to understand what that word means to each person at the table?

For sales engineers or product-leaning folks, ‘enterprise’ may mean lots of customization, extra penetration tests, and filling out lengthy RFP questions about up-time and data privacy. For reps and sales leaders, it could be about targeting companies with a specific revenue size or a certain number of employees and figuring out how to increase velocity in historically slow-moving deal cycles. And for procurement and legal it might be about dealing with more formal, structured organizations—all who want to use their own templates.

‘Enterprise’ — as a concept — really is a snowflake. It inherently means different things to different people.

This is why I was so excited to chat with some of the industry’s heaviest hitters at this year’s Endgame Summit:

• Jessica Arnold, VP of Sales Development at Amplitude

• Renu Gupta, SVP of Revenue at Pachama

• Lauren Schwartz, VP of Enterprise Sales at Fivetran

• Kelly Bray, VP of Account Management and Product-led Sales at MongoDB

These women are experienced GTM operators who have built sales organizations at some of the most iconic companies (i.e. Slack, Twitter, Twilio, Airtable, Amplitude, Fivetran, Box, Dropbox, Vanta, OpenAI, Pachama, and more). Recently, they took their expertise to a whole new level and launched 20SALES, a $5 million fund. So, it goes without saying: each panelist deeply understands the challenges of scaling sales teams. Here’s what they advise for moving up market.

Establish a shared understanding of ‘enterprise’ (and marry it into your systems)

"The reality is: the only way to scale a business and enterprise is to build a repeatable motion. That requires the same language cross-functionally, not just on the sales team." - Lauren Schwartz | VP Enterprise Sales, Fivetran

Before making any real “enterprise” strides, it’s critical to nail down exactly what the word ‘enterprise’ means. Be as detailed as possible. Write it down somewhere everyone can find it.

Carve out time with each department to build a shared understanding. Successfully moving up market starts with consistency, so take any guesswork out of the equation.

Then reinforce those 'enterprise expectations' by baking it into your sales methodology. Reinforce enterprise expectations during regular sales meetings. Mandate that certain fields are complete in the CRM to ensure everyone’s aligned on parameters.

Here’s why that matters. When I joined Loom as VP of Revenue, I walked into a sales cycle with a large retail bank that had already been underway for 12 months. The Head of Innovation was involved, but there were tons of security hurdles that wouldn’t even allow their team to record videos (yeah, not gonna work for a video messaging company). Even after a year of meetings, they hadn't secured a proper demo. It was a complete waste of our time and resources, so we immediately disqualified the lead.

More importantly, we immediately gathered our product, marketing, and operational counterparts, to collectively reverse engineer ‘enterprise readiness.’ We clearly identified an 'enterprise customer base' and then conducted due diligence and research to understand what these customers need to give a 'yes’—everything from administration, security, legal requirements, and analyst support. We needed to know exactly what it takes to sell to these customers on a repeatable basis.

We tailored our P&P, and hired a dedicated PM focused on building out our enterprise capabilities. The goal was not just to have a product that could be sold, but to ensure it was engineered to meet the specific needs of regulated enterprise industries.

For sales, we developed a checklist defining the criteria to engage our executives in a deal. For instance, our VP of Product becomes the champion for deals only of a certain size and complexity, with developed use cases.

This approach isn't just about aligning sales; it's about bringing in the right people from across the organization to speak the same language – to earn the enterprise deal together.

Multithread accounts with quality research and tailored pitches

“We can only win together if we're all willing to step out of our comfort zone and learn more.” - Jessica Arnold | VP of Sales Development, Amplitude

Enterprise sales is much more research-intensive than SMB and mid-market sales—you have to deeply understand each potential client’s business, their industry, and the specific challenges they face.

Plus, you're not just reaching out to one decision-maker—it’s multiple stakeholders across different levels of the organization, to adequately multithread into the business. Because of that, a one-size-fits-all approach won't cut it.

It’s worth taking the time to tailor each enterprise conversation, email, and pitch to make sure your product resonates with their unique challenges. By default, this demands a higher level of skill and preparation. Enterprise reps have to deeply understand the client’s business environment, competitive landscape, and internal dynamics before they can have a meaningful conversation. But once they do, it’s much easier to nurture these enterprise relationships over time, build trust and credibility, and provide continuous value.

Lean on your customer success team

"Post sales becomes more important to you too. Because enterprise is very important for net retention. So you have to think about what does it mean to make these customers successful? How do you keep them for customers for life?" - Renu Gupta | SVP Revenue, Pachama

Once you land an enterprise client, the real work begins to get them sticky for the long haul. Enter: customer retention KPIs and your Customer Success team.

Not only do CSMs help ensure a smooth post-sale transition, but they strengthen the relationship through a deep understanding of the customer’s business challenges, needs, and desired outcomes. That’s why they’re so well-positioned to align your product to your customer’s business objectives over time.  Put simply, a great CS team functions as your eyes and ears on the ground to build the foundation for expansion.

One of my favorite CS + Sales success stories is also from my days at Loom. We got an inbound lead with a well-loved, high-growth consumer tech brand, who was evaluating a global rollout. We closed a $300K deal with them (which was significant for us at that time!), but struggled to influence top-down product adoption.

As we monitored product engagement levels, the outlook seemed bleak. It appeared they weren't utilizing Loom effectively. But here's where our Customer Success team became pivotal. Our Director of CS had fostered a strong relationship with the customer’s tool committee. This relationship helped us align our service with the customer's internal culture and objectives.

Approaching the end of Q3 and our first annual renewal, expectations were grim. Many anticipated churn or a significant reduction in spend. However, to everyone's surprise, we saw significant growth in the account! This success was a testament to how the Customer Success team, by aligning closely with the customer’s definition of success and fostering healthy engagement, played a critical role. It also underscored a vital lesson: success in enterprise sales isn’t about our own assumptions of success metrics (e.g. standard product usage KPIs). It’s 100% about sales and CS working together to meet the customer’s definition of success.

Revisit your ideal customer profile (ICP) often

As you start dealing with enterprise clients, the characteristics that define your ideal customer profile (ICP) will change. These larger customers have different needs, decision-making processes, and expectations. Make sure your ICP reflects the complexities of these larger accounts.

Because as your customer profile evolves, your sales and marketing strategies must evolve, too—targeting the right kind of prospects with the right messages and channels. For example, in a past role, when we were moving up-market we realized our new ICP wanted time together in person to build trusted relationships. So we deprioritized a few marketing tactics that historically worked with mid-market, and instead worked with field marketing to launch intimate salon dinners with execs at these companies.

The key thing to remember is this: larger clients have their own set of needs and ways of doing things. By regularly revisiting your ICP, you make sure everything from your sales tactics to your product offerings matches what your ideal customer is looking for.

Attract early adopters with creative agreements

When just starting out, it's tempting to hyperfocus on every bit of revenue you can get—especially from those first enterprise customers who take a chance on you. But really, growing effectively is about looking ahead.

Early supporters should get some perks (after all, that’s the benefit of jumping in early), but keep in mind that there are plenty of ways to creatively construct agreements. For instance, you might slowly bump prices up over time, expand across different SKUs, or lean into co-marketing rights.

Being able to say, "Hey, look, big names like XYZ trust us!" shows the world that the big players see you as a company worth betting on. And that kind of trust from industry leaders helps attract bigger investments and better partnerships down the road.

Constantly reevaluate the modern customer experience

"Efficiency is obviously critical. But there's also an angle to better serve customers in the way that they want to work with us, which is also more efficient. So that's really a win win." - Kelly Bray | VP Customer Success, MongoDB

Customers today tend to shy away from traditional sales methods like phone calls for every interaction. A lot of the time, they just want quick, easy answers to fix a problem with a product—no call required (or, in their case, even wanted).

Sure, there's still a place for one-on-one, in-depth conversations for the more complex stuff. But for the everyday, repetitive tasks? There’s a better way to meet customers where they already are.

For example, the routine process of sending mass emails—where your team is just copying and pasting the same product update—is something we should phase out. In its place, let’s phase in more customer portals, webinars, or online communities.

These approaches not only make things more efficient but also align better with how customers prefer to interact. Win-win.