Foreword

At EVP, our core investment focus is B2B software. Within this realm, enterprise sales motions feature prominently, and we've been fortunate enough to partner with over 20 enterprise companies on their scaling journeys.

Over the past 12 months, we hosted a series of events and discussions for the enterprise software founders in our portfolio. As much as these founders are often lumped into the general bucket of B2B SaaS, they have very different approaches to go-to-market, hiring, cash management and a range of other issues. 

We realised that there was a wealth of knowledge across the EVP enterprise founder group that could be worthwhile sharing to the broader community.  Over the coming weeks, we’ll be sharing a series of Desk Notes dedicated to exploring common problems faced by founders with an enterprise to go to market.

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Early Enterprise Sales Lessons

The early stages of enterprise software are often veiled in secrecy. Landing your first few sales seems to be a consistent challenge that is rarely documented. Buying journeys are also convoluted, making it harder to get consistent insights that are relevant. 

We spoke with enterprise SaaS founders across the EVP portfolio to try to distil some themes that early stage founders should consider when selling. These founders shared with us their early day sales tips, detailing the learnings from their earliest sales.

Special thanks to the founders who shared their stories with us: 

1. Markus Deutsch (prev. Smartabase, recently acquired by Teamworks - human performance optimisation for sports and military) 
2. Adrian Johnstone (Practifi - vertical CRM software for wealth managers) 
3. Aidan Lister (Uptick - asset maintenance software for fire protection and security) 
4. Shaveer Mirpuri (Insite AI - AI for category planning and revenue growth management)
5. Micah Gabriels (Mooven - construction technology platform) 

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Leverage your existing network

We consistently hear that the first few sales are made through pre-existing relationships or ‘mining’ through your personal network. It’s probably no surprise that what we need the most in those early interactions is simply a bit of trust. Someone you’ve dealt with in the past is more likely to place greater trust in you and your offering.

Think about who in your network might be a densely connected node (someone with lots of connections to other relevant people).

Markus, Founder of Smartabase, tells us, “it was all based on networking in the early days. We were launching in the UK and I managed to get the name of a guy who worked at New Zealand Rugby and then moved to Welsh Rugby. He pulled out a piece of paper and gave me 20 names and 20 numbers, so I called those guys to do a demo and went from there.” 

Looking for referrals through your network is one way to set up trust and warmth ahead of a conversation. You can also make use of your network of investors, advisors and early customers to alleviate the concerns of your buyers. Think about bringing them into the sales conversations when some additional validation may be helpful. 

Aidan, Founder of Uptick shared some of this insight, reflecting on what got his first large enterprise customer over the line after concerns around how ‘new’ the business was relative to other vendors. “They [the customer] got a lot of comfort when our VC came to the sales meeting and assured them that the business was going to be around for a while.”

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Show up where your potential customers are

Adrian, Co-founder of Practifi, believes in showing up where your customers are and finding a way to strike up a conversation as naturally as possible. In that environment, you don’t have to talk like you are selling software. It gave them such a leg up because there were so many opening lines into a conversation that were organic and powerful.

“[Early lead generation] was very relationship based. Find out where the buyers gather. One of the advantages of being hyper vertical or taking a more vertical approach is that people gather in their sub-groups. Wealth advisors etc. can be found at their various conferences / community groups,” Adrian shared.

This is a view shared in a popular blog by Tracy Young, who co-founded PlanGrid (note: not an EVP company). I highly recommend reading her blog as well on early enterprise sales. “We knew that construction folks would spend most of their waking hours on jobsites. And because they were working long hours at physical jobs, we knew they would also be hungry. We would put on hard hats and safety vests and walk straight into a construction jobsite to drop off a big box of fresh local donuts and a stack of our business cards, offering to bring better food for the whole field office team if they invited us back for a thirty-minute lunch-and-learn demo.” Using a bit of creativity in field marketing is always appreciated! 

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Learn the art of selling ahead

One thing that surprised us in conversations with founders was the extent to which they were confident pitching the capability of a product ahead of where it actually was. In some instances, it was barely functional. Hopefully you’ll find a bit of comfort and inspiration from the stories below. A bit of ‘forward-thinking’ could be what it takes to land those first few contracts.

Practifi positioned their first couple of sales meetings as consulting workshops to scope out what the customers wanted… but also to buy time to figure out what to actually demo the customer.

“The client came into our office because they wanted to see the product… but there was no product yet. We set the day up as a consulting engagement so that we could buy time for our engineers to cobble together a barely working instance along with a couple of screens to do what was a 30 minute demo…” Adrian shared.

While the product was more promises than substance at the time, the client was sufficiently sold on the opportunity to work together and hopes for what could be. 

Aidan also shared with us some tactical stories on how to sell ahead. Let’s assume you have a helpful internal champion already. Start a demo off with the high level product (or whatever product you have that can be demoed!) and defer questions about deeper functionality. Try to deflect them to the form of a follow-up or a later meeting. Afterwards, your internal champion can help you uncover what went well and what the key concerns are. Then you can adjust your approach in various ways. Can we promise them that certain features will be built prior to deployment? Can we build something now? Can we show them a wireframe?

“I was literally tabbing between screens to recreate the experience of having a live demo. Ultimately, you should make a high integrity commitment when selling ahead only if you think you can genuinely pull it off and deliver” Aidan explained.

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Teach your customer how to buy

In the early days, InsiteAI figured out that they had an interesting customer problem.

Shaveer tells us, “we have a customer base that is not out there looking to buy a software solution. You can’t simply identify a champion, outline the ROI and invoke a procurement process. One of the fundamental problems is that your customers don’t quite know how to buy your solution, get buy-in from their peers, and evolve for their business processes.” 

So what did they do? They recognised that they needed to teach their customers how to buy the product and guided them through process and internal politics. They prepared a deck, so the CFO could understand the commercial and financial benefits of the product. They taught sponsors how to gently change the workflow of their user’s business teams. They guided other senior stakeholders and how to handle the procurement or IT team’s objections. The more that you can help your buyer navigate their internal buying journey, the less it’s overwhelming and risky for your buyer.

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Dress your product the right way 

Consider 1) what your customer is already used to buying and; 2) how the money flows within their organisation.

InsiteAI realised that their customers were already buying a solution for ‘category management’ problems in the form of traditional management consultants. Knowing this, they chose to wrap the product up as a consulting program (with the software as a feature) to tap into a budget which already existed and lubricate the conversations in their favour. Dressing your product in the right way might help customers gain familiarity with a ‘new’ offering and an easier way in the room. Shaveer is a believer, advising that “this can make it easy for the customer to say yes and gives an opportunity to assess the impact of the solution at the end of the initial contract.” That starting point can be used to reduce friction with follow-on engagements and eventually roll into a more traditional SaaS outfit.

Further to this Shaveer noted that, “you’d be surprised how accommodating your customers will be to your needs if things go well, especially if you show them upfront you are flexible. I told our customers straight up that if we came good on configurations, in exchange, our investors will want to see long-term software licences and the customers totally understood…”

Tracy Young shares a similar perspective, highlighting the importance of finding the ‘right’ budget within an organisation. “We understood how money flowed through the companies and construction projects we were selling to.  We knew that although corporate headquarters technically had a budget for IT and software, it was already maxed out to pay for legacy solutions. Construction projects have their own independent accounting silos, so we could skip the buyers at the corporate office completely. We knew exactly which line items we could tap into. For example, ten percent of many construction budgets was slated to “random allowances” and another ten percent to “contingencies.” We targeted our end users at the individual level, folks who have never purchased software in their lives but had jobsite buying power.”

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Manage your pilots carefully

Pilot programs can be an effective way to build your credibility amongst potential customers. Founders consistently warn us to keep some checks and balances in place to ensure you get the most out of it.

It’s important to clearly identify the desired outcomes with your customer. From there, you can work backwards to develop a plan to achieve those goals. As the pilot progresses, be sure to track and document the return on investment on a regular basis. This not only helps to reduce any perceived risks for the customer, but allows you to clearly demonstrate the value generated by the pilot program over its duration.

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Founders' perspectives on pilots

“We moved away quickly from POCs and free trials. Never turned back on that. If the customer is not committed, they only perceive a fraction of the value. We let them cancel if we didn’t deliver.” — Micah Gabriels

“If they don’t pay for it, they don’t value it. Get yourself on the books for something. We would ask a customer to pay $99 a month as a starting point, it forces everyone to get serious. The act of them going to the CFO to start the buying process is way better for us. Never do a free pilot. I’d rather close it as an opportunity than to let a free pilot sit there forever.” — Aidan Lister

“We couldn’t offer free pilots even if we wanted due to the cost of a Salesforce instance. Instead we took an approach of premium level pricing discounted. Rather than base level pricing scaled up over time. Be ready to budge on price but try and get something else out of it like a multi-year agreement. Obviously the first cohort of customers got a better deal though” —Adrian Johnstone

“In the early days you honestly just want to sign anyone you can any way you can. Today, we hardly ever use discounting or sweetheart deals. We found that most of the clients who we gave those sweetheart deals too (pilot or otherwise) were bad clients. They didn’t value it because there was no skin in the game… everybody loses enthusiasm” — Markus Deutsch

“At InsiteAI we had an approach of no free pilots. Instead, we tended to extract from their budget pool historically used to solved the business problems we addressed. It’s the budget they had anyway. We’d ask: “were you going to spend on BCG? Let us be the partner instead”. This meant early contracts were not beautiful software licences, but it works because you’re slotting into the way the customer buys” — Shaveer Mirpuri

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Desk Notes is a new series of insights from our experience working actively with over 40 SaaS companies. You can find more of Allen's thoughts on tech through his Medium or on Twitter.