How to Sell a Multi-Million Dollar Enterprise Product to a Technical Customer

After over eight years of hosting our monthly New York Enterprise Tech Meetup (NYETM) and bringing together the enterprise tech community of Fortune 500 execs, enterprise startups, and investors in NYC, we held our first-ever virtual meetup this past week.

While there’s no replacement for the in-person connections at our meetup, going virtual gave us the amazing benefit of extending beyond our NYC audience, with attendees from the West Coast, Canada and even Europe joining us.

This month’s NYETM focused on something we often hear from our enterprise startups — many of whom are building tools and platforms across data, infrastructure, DevOps, and more, which require highly complex and technical sales:

A lot has been written about SaaS and high velocity $30K deals. But what is different for a multi-million dollar enterprise sale — especially a highly technical one?

Our NYETM panel featured three enterprise sales leaders, including Rick Underwood (VP of Sales West at Snowflake), Laura Ripans (Director, Channels & Alliances at Datadog) and Katie Porter (Sales Engineering Lead at Tamr) as they shared key tactics for selling a technical enterprise product:

People

“It’s easier to find the people who can say ‘no’ than the people who can say ‘yes.’”

There are often more people who want to say no to your product, than yes. To find those “yeses,” you’ll need to understand various levels of needs within the potential customer’s organization, even beyond the MEDDIC champion, end user, and sponsor:

• What are their technical pain point(s)? Who is benefiting from this deal on the technical side? Go to these people first.
• What is the business buyback they’ll need to secure a contract? Who is benefiting from this deal on the financial side? Rick talked about the importance of his sales team at Snowflake knowing the TCO/ROI of their platform to pitch to prospects.
• Who are the additional stakeholders hiding behind the scenes who are involved in any multi-million dollar deal for the organization?
• What has this customer purchased in the past? For example, many engineers have never made a purchase, nor do they have the power to. So you’ll need to push your net wider into the organization to find the actual buyer who has purchasing power.
• Does this customer have a particular buying approach? Are they more comfortable buying from channel partners? These partners may have a history with the customer, know how the customer likes to spend money (what their comfort level is), and be the key way into a customer, in order to reduce sales friction.

Specifically for technical products, you might need to work with people up and down an organization’s food chain and you shouldn’t discount anyone based on title alone. For example, Tamr’s sales team works with data scientists, corporate managers, CIOs, CTOs, among many others.

One approach to customer introductions is “Middle Out GTM.” Work-Bench’s Jon Lehr dives deeper in this strategy in a blog post and explains:

“Often this person is still growing in their career, and meaningful wins don’t just help their company address a pain point, they help this individual stand out from the crowd to continue their upward mobility. When you can find somebody who is senior enough to own a pain point and the budget authority to solve it, you’ve struck gold. Given the potential positive career impact, they’re incentivized to spend meaningful time if your startup is uniquely positioned to help them.”

Product

“You can’t just rely on a flywheel [self-service] approach because there is no feedback.”

We know for developer and infrastructure platforms, it is very tempting to want both a self-service model (where developers or users can use the product just by swiping a credit card) as well as a traditional enterprise sales team. After all, self-service should be easy, right?

While a self-service model may seem like an easy way to pull in technical customers right off the bat, it’s actually very difficult for early-stage startups to pull off successfully, as it requires:

• A robust marketing outreach program to draw people in
• Oftentimes salespeople to shepherd these customers through the sales cycle to get to those multi-million contracts
• A PoC and a sales engineer to make sure that early stage friction in the product is removed (otherwise, you’ll lose a lot of customers in this early stage)

And customer feedback is critical in the early stage of a product as it drives how quickly you can get to the product-market fit and iterate on it. With self-service, there is no feedback loop.

Related, we discussed the importance of building a relationship between your sales team and your product team:

• It’s best to include a product person in the sales process after the early stages of the sales process (likely right after you finish a PoC or PoV, “proof of value” as they call it at Datadog) as this is likely the time you’ll receive customer feedback and need to make product improvements. Your product team will be able to understand this feedback more deeply and best negotiate the deep engineering and technical product aspects.
• Put a process in place to smoothly and quickly engage product managers when / if a customer comes up with a deal breaker, even if this means delivering a beta version to gain beneficial feedback and understand their need more deeply.

Process

“Procurement are people too.”

Anyone who works in enterprise sales knows that getting the “yes” from your buyer is sometimes only half the battle. The other half starts when you go through procurement at a Fortune 500, which can be a grueling and opaque process. This is especially acute for technical products related to infrastructure, cloud, and security — where MSAs, third risk assessments and vendor risk management requirements may be even more scrutinized.

A good reminder: “Your sales team needs to be students of your business and understand your contract and security policies to set expectations upfront. It’s not your lawyer’s obligation to understand this, it is your sales team’s.”

Sales can get held up for months if not approached with a tight plan of action, so stay ahead of procurement with a documented “win plan.” A champion customer will understand the need to keep procurement on track and help you get as much done in advance as possible. Top items to tackle:

• It’s important to get to procurement yourself and make sure you’re getting consistent messaging. If your champion doesn’t have that consistent messaging, then they may not be the champion, they may only be the supporters.
• Ask if there is a vendor risk assessment required and complete it asap.
• Have a data security and protection plan in place.
• Be honest about your price points and possible discounts. Understand what motivates your customer, as sometimes procurement teams are incentivized and paid to knock off some contact dollars.
• Set a specific end date and drive towards it with your customer.
• Work with different partners who bring credibility and trust to the customer. This may mean channel partners.
• Review your win plan frequently and make sure you’re on track.
• Share and aggregate success criteria at the start of any agreement to manage expectations.

See a full recording of our webinar here.

Thank you to Kira Colburn for her work on this piece.

If you’re thinking through enterprise sales during this time, check out our Work-Bench Enterprise Sales Guide: COVID-19 Edition, with top guides, resources, and advice from enterprise founders and revenue leaders.

If you’d like to talk through your GTM strategy during this time, email us here to join an Enterprise Sales Chat.