The sales process for almost every software company begins as product-driven and founder-led. Even sales-savvy founders can struggle to meet the needs of and successfully sell to enterprise clients, as moving upmarket increases the complexity of both the product requirements and sales process. The mindset and approach needed to execute on an enterprise sales strategy encompasses a strong understanding that customization is the centerpiece of every enterprise deal. Building a well-structured, enterprise-ready sales organization is an indispensable part of making enterprise sales a sizable portion of your company’s business.
Here we delve into how to build a successful enterprise sales team, with an emphasis on best practices and some common pitfalls to avoid.
Ensure that your organization really is ready
Mistiming your foray into enterprise sales is deceptively easy. Start too soon and your product isn’t ready, resulting in lost opportunities; start too late and miss out on potentially game-changing partnerships and revenue streams.
Have you nailed product-market fit yet? If you’re not sure, or are still iterating in one of the many cycles typically required to validate PMF, then you might not be ready to pursue enterprise clients yet. Wasting time on prematurely pursuing this type of customer is costly, as is making poor first impressions on your target enterprise clients. Don’t put too many resources into developing enterprise sales before you’ve generated sufficient demand.
But don’t wait too long, either—under-investing in an enterprise sales strategy, especially as a software company, is not “saving” you any money. Startups that don’t ever prioritize building their enterprise sales competencies miss out on the likely lucrative contracts and valuable visibility to be had by providing solutions for Fortune 500 companies.
Regardless of where you are in the product lifecycle journey, your organization is much more likely to succeed at enterprise sales if your product or service is highly customizable and adaptable. The needs and requirements of enterprises are always unique, and from the perspective of an enterprise, your product is the most valuable and useful if it can be changed.
Do things that don’t scale
The core of any great enterprise sales strategy is its people, starting with the company’s founder. To land those early sales with your target enterprise clients, you can and should feature the developer-led focus of your organization to emphasize your team’s ability to customize your product. Maybe, as you adapt your offering to meet your enterprise clients’ specific needs, you can even permanently improve your product or service based on their valuable input. In the early days of selling to enterprises, you can also engage in other high-cost customer acquisition activities—like traveling for meetings (in non-pandemic times), organizing educational seminars, leading focus groups, and providing additional customized documentation. At that beginning stage, you even have time for personalized, thoughtful gestures like sending handwritten holiday cards.
Choose your first hire carefully
If you’re a true evangelist for what you offer, and effective at making the first few enterprise sales, then inevitably you will need to hire an enterprise sales “rockstar” to build upon your initial success. Your average enterprise deal size and rate of enterprise dealflow dictate when it makes financial sense for you to hire the first member of your enterprise sales team.
The transition to entrusting another person with generating enterprise sales can be fraught, logistically and emotionally, for founders. That first hire, like the founder, should be immensely passionate about the business and also explicitly empowered to challenge the founding team when necessary. Much like the founder, too, the first person on your enterprise sales team is forging a new path with every new outreach to an enterprise client. Much more than just a salesperson, your first hire must be a great communicator, problem-solver, capable of juggling multiple priorities—and willing and able to meet sales quotas. Most important is being able to sort through many low-value leads to identify and stay focused on the most profitable and likely enterprise prospects.
With your team of one on board, you can initially continue to prioritize inbound leads, especially those sourced from partners or your network directly. After gaining traction with inbound inquiries, you and your tiny team can then develop and pursue an active outbound marketing strategy.
“Land and expand” to grow revenues
Start engaging in outbound marketing by testing out a few potentially viable tactics, while keeping a focused “land and expand” mindset. Your initial goal with any potential enterprise client is to land a starting engagement, even just a small pilot project—and then continually and incrementally expand what products or services you provide. The best way to steadily expand your engagement is to consistently “wow” your client with your product’s usefulness and adaptability.
Repeatedly “landing” and “expanding” is the most effective way to steadily grow your revenue, provided that you continue being willing to start small with every new enterprise client. And be prepared to grow your enterprise sales team, because as your client base grows, you will need to hire additional staff. These are important hires, too, who must understand from the outset the value of customization to enterprise clients. The personalities of these sales professionals matter as well; the enterprise sales cycle is notoriously long, making enterprise sales highly relationship-oriented rather than transaction-driven.
Provided that you have the demand, you can begin to scale your enterprise sales team as soon as your initial hires develop and become proficient with the sales process. When scaling the sales team, an organized approach is best because it replicates the most easily as you continue to add team members. From the outset, you can structure the sales team by product, function, or geography, and continue adding divisions as the team expands.
One pitfall to avoid is hiring dedicated customer service professionals too soon. Customer service is a function that, while important, is often over-invested in by many organizations in the early days. The sales team itself is usually well positioned to provide excellent customer service to the first enterprise clients, and those early resources being spent on dedicated customer service would be better used to pursue new outbound marketing leads.
Your team will evolve, as will your product and clients, as you and they grow. You can eventually add team members focused only on customer success, and you’ll want to ensure that your organization’s legal counsel can address any enterprise-related issues that may arise. No matter what, as you grow, stay focused on what’s most important to your enterprise clients—adaptability and responsiveness.
Use data to evolve your sales process
Trusting your gut instinct is a key component of hiring and leading your enterprise sales team, but data plays an important role, too. You can and should collect data to perform targeted analyses; doing so will provide valuable insights into the strengths and weaknesses of your enterprise sales process.
Plenty of basic sales metrics—like monthly or quarterly revenue, the rate and cost of acquiring new customers, and your upsell success rate—provide useful information. Consider which metrics are most appropriate for your business, and collect the relevant data accordingly. The collection and analysis of data, alongside the modification of your sales approach based on the data’s findings, should be held up as core values for your enterprise sales team. The quantitative findings may be surprising, unwanted, or inconvenient, but the data (usually) doesn’t lie. Adapting your approach to enterprise sales based on your findings is a necessary—if sometimes challenging—component of achieving enterprise sales success.
Robust data collection and analysis and a commitment to adapting your approach based on the quantitative results should lead to the emergence of best practices for your sales team. These best practices can then be positioned as core tenets of the organization’s selling strategy and shared with all future members of the enterprise sales team.
Nail it, then scale it
A common ethos among tech startups is that “failing fast” is preferable, because it preserves your ability to pivot unscathed and try again. While that attitude may prove useful when you are just rolling out your go-to-market strategy, such an approach could be too risky when pursuing enterprise clients.
“Nail it, then scale it” is an expression that imparts the importance of establishing an effective enterprise sales strategy before attempting to scale your efforts. High-paying contracts with large enterprise clients will always be in short supply, which is what makes those first impressions so important.
Staying small while you learn what your enterprise clients value most makes it easier to try something, test it, analyze it, iterate on your approach, and try again. Keep improving until your enterprise sales process is both structured and flexible enough to meet all of your enterprise clients’ needs. Then—and only then—aggressively seek to expand your enterprise sales efforts.