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We recently had the pleasure of sitting down with Ben Orenstein to chat about his experience in Enterprise Sales. Ben is the co-founder and CEO of the remote pair programming app Tuple, and has an impressive history of creating useful apps and tools for developers and non-developers alike. Watch the full interview below.
During this conversation we dig into what Ben has learned in Enterprise Sales process, where he sees the low-hanging fruit with expansion opportunities, and what’s surprised him most along the way.
Psst! Tuple is looking to hire a great B2B salesperson to build out and lead their sales team. Learn more about this opportunity in the interview, and apply on their site if you think you’re the person for the job!
When we think of Enterprise Sales, we tend to think of long sales cycles, complex contracts, and large deal sizes. But what does that really look like for your business?
Ben would argue that you’ll know it when you see it.
Rather than designing an Enterprise Sales motion and then setting out to find leads, Ben noticed specific requests and needs coming from large potential customers and developed a sales motion to close those deals. Those requests generally fit into two categories: product needs and process needs.
Enterprise Sales usually involves an expanded use of your product or service, and this comes with specific requirements from the customer.
The biggest differentiator in an enterprise plan at Tuple — and many software companies — is Single sign-on (SSO) Support, which allows people to use one username and password to sign into multiple applications. (Ever had the option to log into something using your Google or Facebook account? That’s SSO.)
☝️ Tip 1: Each industry has unique product needs for enterprise customers, and paying attention to requests that you’re getting from large customers will help identify your offerings for an appealing enterprise plan.
As customers invest more into adopting your product or service, they often take extra steps to validate their decision and reduce risk during the purchasing process.
At Tuple, this came in the form of “bespoke Excel spreadsheets with hundreds of questions” for security audits. Lots of them. And while this was not exactly where Ben wanted to spend his time, he learned that it was a telltale sign of an interested enterprise customer — and some ways to make the process a little less painful for everyone involved. Keep reading for more on that.
Enterprise Sales often requires redefining who the “customer” actually is, since there are multiple stakeholders throughout the sales process. Is your customer the person using your product or service? Are they the one signing off on the contract? Who’s entering the payment details?
Our conversation with Ben highlighted 3 important roles you might encounter: the end user, the budget manager, and the trained negotiator.
The end user is the person actually interfacing with your product or service. At Tuple, these are software engineers who use the product to pair program. However, your end users could encompass a broader category of people depending on the various use-cases for your product or service. For example, Streak can be used to track sales leads, raise funds for a startup, track job applicants… The list goes on, and the end user varies.
For smaller or SMB Sales deals, end users usually make up your customer-base and will happily purchase via self-serve with very little sales effort. In Enterprise Sales, your end user will often be a champion for your product, but not your decision maker. Even if they’re not signing on the dotted line or making the payments, it’s important to understand the end user’s needs and offer them a great experience. Once they’re invested in using the product or service, it becomes more difficult for the person approving the budget or negotiating a contract to walk away without a deal.
☝️ Tip 2: Gain a clear understanding of who your end-user is and what role they play in the purchasing process. Developing customer personas can be a great way to do this.
In medium-sized deals, the person who manages the budget for a specific part of an organization is typically your decision maker. For the Tuple product, the budget manager would be the director of engineering or a CTO at a software company.
Their decision is often based on their allotted budget and comparing you to competitors to hone in on a price range. These stakeholders can be the decision maker in Enterprise Sales negotiations for medium-sized enterprise customers.
When the budget manager is your decision maker in an enterprise deal, they’re often responsible for both negotiating the contract and implementing the product or service, so closing the deal becomes a matter of helping them manage that project.
☝️ Tip 3: Make the purchasing and implementation process as easy as possible for this decision maker to provide a better experience for everybody involved — and help you close more deals. Keep reading to see how Ben approaches this.
Enter the “procurement person.” Often known as a “supply chain professional” or simply a “buyer”, this person is tasked with negotiating and closing contracts. Beyond conducting due diligence for all of the company’s purchases, Ben notes that “they’re trained and possibly compensated or evaluated on their ability to get discounts or other concessions.”
Since they’re tasked with getting the deal done, they typically have a no-nonsense approach. In Ben’s experience, once you start working with a procurement person, “it’s almost not negotiation at that point. It’s [more] like, ‘you want this and we’re going to find a deal structure or a set of terms that works for both sides.’”
Not every enterprise customer will have a dedicated procurement person, but it’s something you’re bound to encounter once you start landing larger customers.
☝️ Tip 4: Be prepared to discuss and negotiate your deal structure by knowing where you can give up ground and where you need to stand firm. See below to learn what levers Ben uses in negotiations.
Ben’s experience with Enterprise Sales opportunities was “if you build it, they will come.” Tuple is designed for teams and focused on a high-quality user experience, so larger deals started knocking on the door as soon as user adoption picked up.
In our interview, we discussed how Tuple generates inbound leads, as well as Ben’s (strong) opinions on cold outreach and the low-hanging fruit of expansion opportunities.
Whether you’ve got a large marketing budget or are relying on word of mouth, you’ll need to create some buzz in order to generate inbound leads. The best way to do this without a dedicated marketing team? Share with your community. Ben is active on Twitter and was able to generate a decent amount of awareness by word of mouth.
The other tools in his arsenal are podcasts. Ben regularly produces his own podcast, The Art of Product, and also engages with industry folks on their podcasts and shows.
☝️ Tip 5: Starting a podcast is a great low-cost and low-overhead way to establish your brand authentically and share your unique perspective on a niche subject.
There are many ways to conduct outbound Enterprise Sales. In this interview we discussed email outreach since it’s a common and low-cost way to do outbound sales.
We’ll cut right to the chase: Ben dislikes receiving cold emails (don’t we all?) so he doesn’t send them. Beyond personal preference, he has two main reasons why.
The first reason is that cold outreach can require more education. Your target may not even be aware of the problem that you’re solving before you reach out to them. For example, Ben may have to convince engineers why they would want to pair program before he can demonstrate how Tuple will help them do so.
The second reason considers Tuple’s adoption model, which is bottom-up and begins when one or two developers try the product. Outreach targeting the decision maker is less effective in this case, because CTOs rarely mandate which tools their team should use for things like pair programming.
The key to overcoming these challenges is research and a little creativity.
Rather than casting a wide net with hundreds of generic prospecting emails, identify leads with a specific need for your product or service. Take the time to understand the problems they’re facing and demonstrate how they could solve them with your product or service.
☝️ Tip 6: Outbound sales can be productive, but make sure you do your research to understand who the stakeholders are, how your product or service is typically adopted, and what problem you’re solving. Once you do this, you can get creative with the best way to connect with decision makers. A good cold email should be well-researched, personal, and clearly convey the value that you’ll add.
Expansion opportunities fall somewhere in the middle of the inbound-outbound spectrum for Enterprise Sales. Given Tuple’s typical adoption model of a few engineers trying and championing the product, they’re also seemingly low-hanging fruit.
Imagine you notice hugecompany.com sign themselves up for three seats of your product. It doesn’t take much imagination, or research, to know there’s a well of untapped potential there. The question becomes: how do you incentivize those three people to become your “outside sales team” within their own organization? Maybe you send them t-shirts or offer other referral incentives. There’s a ton of room to get creative here.
☝️ Tip 7: Tools like Clearbit can help you learn how many employees your customers have and where there’s potential for Enterprise Sales expansion opportunities.
Ben learned quickly that most things are negotiable during the Enterprise Sales cycle. In fact, it was one of the things that surprised him initially.
There are a few levers that he uses when negotiating with enterprise customers.
Remember those bespoke Excel spreadsheets that Ben got for security audits? Yeah, well, he doesn’t fill a lot of them out. And he still closes many of those deals.
Instead of dedicating resources to filling out individual security audits, Ben put together a comprehensive security page on their website. Now when he gets a security audit, he directs leads to the web page and estimates that 60% of the time this meets the customer’s needs. For the remaining 40%, “if they have any questions leftover, they let me know… but the ask almost always shrinks.”
☝️ Tip 8: Identify ways to efficiently fulfill customer requirements during the purchasing process, like creating resources to provide data or answer questions at scale.
In his quest to automate things and maximize efficiency, Ben accepted, begrudgingly, that even an engineer can’t program their way around the Enterprise Sales process. You just need a human to do some of it. But while you’re at it — you can negotiate.
In fact, Ben uses the fact that humans have to do this work as a lever in his negotiation. “If we’re going to go through all this negotiation,” he asks, “why don’t we just change this one-year agreement to a two-year agreement or a three-year agreement? Or… why don’t we just throw an auto-renew clause in here, and also the price is going to go up 5% and we just agree now?”
☝️ Tip 9: Don’t save the renewal conversation until their contract is expiring! Get out ahead of renewals by offering to save time on future negotiations.
Each product or service will have their own margins to play with for pricing negotiations. In software, Ben acknowledges that “at the end of the day, all deals are profitable for us,” because the marginal cost is so low.
At the end of the day, Ben finds that having a little wiggle room on pricing may end up making his life “easier in other ways, like [negotiating for] longer agreements, auto-renewals, [and] elevator clauses.”
☝️ Tip 10: Go into pricing negotiations with a clear understanding of what your asks are, like auto-renewals or price increases, and what you’re willing to move on.
If finding creative ways to close deals at Tuple sounds exciting to you, be sure to check out their job posting and apply directly.
We’d love to hear what you’ve learned in enterprise sales! Share your own tips below👇.