8 Go-To-Market Tactics Every Enterprise Founder Needs to Know (That Can’t Be Found on Blogs)

Highlights from our Work-Bench Enterprise GTM Summit

Jonathan Lehr
Jun 12, 2019 · 10 min read
Work-Bench Enterprise GTM Summit

At Work-Bench, we’re laser focused on helping founders launch and scale their enterprise go-to-market efforts.

Despite all the blog and video content out there, landing Fortune 500 enterprise customers in a scalable and repeatable way is arguably more challenging than ever.

This is where we spend a majority of our time with our portfolio companies — between curated intros to the right buyer at the right time, to working with founders to determine the best sales motion for their business, to assisting in hiring a sales team when the time comes.

Since every enterprise founder faces a similar challenge and in an effort to connect a community of folks slogging through the trenches together, we were thrilled to host our Work-Bench Enterprise GTM Summit last week in SF. The Summit brought together 50 curated seed funded enterprise founders nominated by top west coast VCs to share some of the enterprise knowledge we have gathered from our 200+ events a year here in NYC and bring it to the west coast.

From our experience, most enterprise founders know the basics, but there is no “one size fits all” GTM strategy. The hard part about enterprise GTM is not the 101, but rather the 202 that is challenging — where once you get the sales motion going, there feels like countless places to optimize. So much of enterprise sales has to be learned and experienced directly. It’s why our agenda focused on open and honest stories from founders and executives who have been through it all, to share their top lessons and learnings from their own enterprise struggles and challenges.

Our speaker lineup included:

  • Bob Tinker, founding CEO of MobileIron who led the company to its IPO as CEO. He captured his journey building and scaling MobileIron through his book Survival to Thrival and talked about the elusive “Go-to-Market Fit” that enterprise founders need to find.
  • Jaimie Buss, VP of Sales at Zendesk, talked through sales strategy and processes that helps her forecast revenue to 1% accuracy. Jaimie has sold everything from SaaS to virtualization, storage, and networking through sales leadership positions at VMware, Coverity, and Meraki.
  • Tim Eades, CEO at vArmour, who previously sold Silver Tail to EMC, shared his “hacks” around procurement, PO, and security and legal review challenges that comes with every enterprise sale.
  • One of our most popular sessions was our Corporate “AMA” Roundtables — where founders building Cloud, Security, AI/ML, and Future of Work startups could get face-time with executives at Fidelity, Bank of America, Unity Technologies, Cloudflare, and Zenefits about their top priorities and successful tactics to navigating and closing large enterprise customers.
  • We closed out with a fireside chat with Yvonne Wassenaar who earlier this year joined Puppet as its CEO. Yvonne was previously CIO of New Relic and she shared her perspective from both sides of the table — as an IT buyer and now as CEO of a devops company.

While we can’t share all the details from the day given the Chatham House rules we imposed to facilitate a truly open conversation, here are the top 8 takeaways from our Enterprise GTM Summit:

1. GTM-Fit is the missing piece in many enterprise founders’ journeys

Why do so many B2B startups get to product-market fit but then never unlock growth?

Product market fit is a huge milestone but not enough to unlock growth. Go-to-Market fit is the missing link, and this is especially true for the Seed II and Series A startups we work with here at Work-Bench. GTM-Fit is the transition from founder-hero selling to a repeatable growth machine for winning customers over and over again.

Many mistakes in finding GTM-Fit were discussed, but a few that stuck out were as follows:

  • Founders cannot find GTM-Fit. You can get meetings that regular sales people can’t and say things that the sales people can’t. What you’re doing is not a real test of the real world. This is hard for founders to hear, but you are your own worst enemy for finding repeatable GTM.
  • Another common pitfall is hiring for VP Sales too soon. No top VP Sales will be the first sales person in the building. The thing a good VP Sales does is figure out what is working and what is not, whereas early GTM sales reps are part sales, lead gen, and product marketing. You need a “Davy Crockett” who can find the path through the woods by trying different methods and messaging.

Bob Tinker wrote the book on this topic and we’d highly recommend buying Survival to Thrival: Building the Enterprise Startup as it dives deeper on all things GTM-Fit.

2. Learn (and Validate) From Your Early Customers

In the early days of your GTM, you need to be absolutely methodical about learning from every customer interaction. A helpful exercise is to take 20 deals and grind through every detail to find GTM Fit patterns. Create two columns and list out what got customers to keep talking to you on one side, and on the other list out what you thought would’ve worked in your messaging but actually didn’t resonate. Aggregating these learnings around winning and losing is critical in the early stages before you ramp up your GTM further.

3. Confirm “Do Nothing” Is Off the Table

This is most frequently a startups’ greatest competition: a prospect simply sitting back and doing nothing.

It doesn’t matter if you have the technical win and were selected as a vendor of choice, if you don’t have sign off from the executives that there is budget and a desire to act this quarter. Finding someone who has the budget isn’t sufficient — you need someone who can move budget too!

If you’re in the middle of the sales cycle, you can be straightforward and simply ask your prospect “Why would you buy my product in this quarter?” to see what they say. By whatever means necessary, you need to confirm that “do nothing” is off the table before proceeding in your sales process.

4. The Puffer Fish Effect

Especially in the early days of a startups’ GTM journey, customer prospects may use the startups’ small size and immaturity to negotiate the cheapest deals for themselves.

It’s important for startups to meet this head on and be upfront with customers, even if it means that in theory they’d cost more than a prospect’s existing solution. The key is listening to a buyer’s criteria and then using levers that are important to you in order to get a win, even if it means a discounted deal.

The trick is trading the discount for something to make you look bigger than you to the next customer, hence the puffer fish effect. You want to make the most of every single win and amplify it as much as possible. This can be logo usage on your website and marketing collateral, reference calls and written testimonials, multi-year contracts, payment terms for upfront cash, and more.

5. Customer Sequencing is Key

This is something that we live daily at Work-Bench as we engage with our Fortune 500 network of corporate executives. The more time you spend in enterprise technology, the more you see firsthand that within certain industries, sequencing is key. Whether it’s selling to Wall Street and knowing which banks tend to move quickest and also unlock respect from their peers, or in telco knowing who you need a logo and stamp of approval from before going to everyone else.

We named names in this session that we can’t blog about unfortunately, but this is an important dynamic you should push your VCs and advisors on to make sure that when you’re an early stage startup with limited runway and bandwidth, that you prospect the Fortune 500 in the most efficient manner.

The other related point here is industry sequencing too. Many of the speakers during the day confirmed our view that some industries (financial services, pharma, media) tend to be much quicker, more sophisticated and have greater buying power than others like retail which tend to be too protective of their brands, face many blackout dates for software rollouts, and don’t have the most sophisticated teams evaluating emerging technology solutions.

The last nuanced point is that even within early adopter buyers, there is also a sequence to the stack that they buy. Knowing what product categories get bought before others in your domain, and making sure that you’re pitching prospects at the right time in their journey is an important consideration.

6. Know Who Your Demos Are For

Demos are about demonstrating that you can solve a customer prospect’sproblem. Too many startups are desperate to demo their technology, and this is wrong.

The demo isn’t about finding their problem. It’s about showing your solution to their problem. You should have already agreed to what problem they are trying to solve, and that it’s big and growing. Use Powerpoint to tell them what they are about to see, and afterwards remind them what they have seen. This reminder is critical, especially if they’re on the phone.

The same goes for making sure that your POCs/trials solve their problem too. Have success criteria around their problem list (3–5 things) in a slide at the executive readout. After the POC, list the 10 things you did to solve their problem (don’t find new ones, but fragment the ones they have) and you’ll be a hero.

7. Supercharging Your Orders

In each contract, provide a time-based opportunity to expand. Yep, you heard that right. Even if the customer didn’t ask for it and claimed to have a limited budget to get going.

For instance, add terms to your contract for how an account can grow within 90 days. This can be selling more product at a greater discount, or expanding to more datacenters if they roll it out quickly. Sometimes a business owner will see the economies of scale and if they really believe in your offering, it can help supersize the deal.

Another tip is spreading money between two financial years and ramping your deal between them. Especially when companies’ fiscal years don’t end Dec 31, this is a nice tip to unlock access to two budget cycles and increase your deal size.

8. Neither Bottoms-Up Nor The CIO Is a Silver Bullet

Bottoms-up adoption is all the hype today. The trick when selling to the Fortune 500 though is pairing this with both messaging, outreach, and product features for mid-level managers too. If an Engineering Manager sees their team beginning to adopt a new product, if a startup proactively reaches out to them and explains how they’re enterprise grade and has functionality like reporting which can make a manager’s life easier, it can help them beat out the competition and earn their support.

From the other end of the spectrum, some companies still try and go directly for the CIO. They’re no longer a buyer for the majority of things a startup would pitch. So instead of trying to reach the CIO, make sure you’re going 1 or 2 levels down. This is where functional leaders actually have pain points with budgets to solve them. If you can align yourself with their “Top 3 Whiteboard Problems” to solve for the year, this can help ensure you’re solving a high priority problem that has urgency — they need your help in order to meet their goals for the year and get their bonus.

If your product isn’t in the top 3, chances are your product is not getting bought this year. It is far better to know this early on than to spin your wheels. Move on to the next prospect, while nurturing this prospect for next year.

Like These Enterprise GTM Takeaways? Reach out!

This is just a taste of some of the discussion topics from our half day Enterprise GTM Summit. We covered so much more than we can cover here, and got into the nitty gritty of legal, procurement, EULAs, sales processes, “naming names” of good and bad Fortune 500 company behavior, and more. If you’re an enterprise startup just beginning your GTM journey, we’d love to connect and hear how you’re thinking about landing your first few customers.

As early stage enterprise technology VCs focusing on Seed II and Series A investments, this is an area we at Work-Bench are passionate about and focus on helping our portfolio founders navigate on a daily basis, between curated introductions to customers and strategic guidance around these points discussed above and lots more.


Work-Bench is an enterprise technology VC fund in NYC.


Work-Bench is an enterprise technology VC fund in NYC. We support early go-to-market enterprise startups with community, workspace, and corporate engagement. Sign up to get our digest of top content & industry news weekly: work-bench.com/enterprise-weekly

Jonathan Lehr

Written by

All enterprise tech, all the time || VC @Work_Bench, Founder of @NYETM, and @KauffmanFellows Class 19 || I also tweet (a lot) about the @MiamiHEAT


Work-Bench is an enterprise technology VC fund in NYC. We support early go-to-market enterprise startups with community, workspace, and corporate engagement. Sign up to get our digest of top content & industry news weekly: work-bench.com/enterprise-weekly

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