Thriving in Tough Times: Selling to CXOs – What Works & What Doesn’t in a Tougher Economy

This is part six of the Mayfield series, “Thriving in Tough Times: Expert Insights.” In this series, we will share key takeaways and lessons learned from experts across a variety of fields. Stay tuned for content on reputation management, leveraging marketing, leading in challenging times, sales strategy in times of crisis, pivoting field marketing to digital, and more.

Selling is already a challenge for many startups, and the current crisis is placing an added burden to have a much clearer story on a startup’s offerings. A tougher economy requires pain-killers (must-have solutions) and not vitamins (nice-to-have solutions), so companies must demonstrate that the benefits of their innovative solution far outweighs the risks of working with a startup in these troubled times. To better understand what works and what doesn’t in this environment, this week’s Thriving in Tough Times installment featured 3 expert panelists who shared real life best practices. These experts have been in the trenches with startups as customers and shared their expertise for how a startup sales team can engage and win early customer adoption. Our experts were Alan Boehme, VP of Innovation – Digital/Information Technology of Procter & Gamble; Brian Lillie, former Chief Product Officer & CIO of Equinix; and Mark Settle, former CIO of Okta.

Here were some of their key takeaways:


First Meeting Strategies

  • Leave a meeting with people wanting more – you don’t have to exhaust everything during that time. You’re doing something revolutionary at Corp X, and they want to hear more about it. Sharing a lot about vision helps.
  •  Develop some degree of personal empathy with your audience – get quotes about pain points from other customers (they don’t have to be high level people), and ask your customer about their needs.
  • Engage directly with their product, company or offering to bring direct experience insight before you talk to them – then show that connection to the brand in your deck. You really want to develop that human-level relationship.
  • Separate hard benefits from soft benefits. Displacing a competitive vendor, for instance, by saving money is different from saving 10 minutes of time for each warehouse worker, so be careful how you quantify things.
  • Offer a process for next steps, that is your refined methodology for ensuring value and impact, and ask for their buy-in into the process.


What Corporate Buyers are Looking For

  • Vision – Even if a startup doesn’t have much going on today, what is their vision for tomorrow?
  • Secret Sauce – Some spaces are supersaturated – what is your secret sauce? There has to be some kind of technical differentiation you’re going to bring to the table.
  • Business Credibility – Do you have existing customers, or even alpha customers? All too often when salespeople pitch, they only know 3 examples. They don’t do their homework and look at the buyer’s business model or business problems.
  • Competitive Landscape – It’s helpful when startups position themselves. No one wants to ask 20 questions about where your company stands. Admittedly, the startup will put their spin on it, but at least it’s a starting point.


The Network Effect – Advisory Boards

CIOs are a very connected group, and the number one way to get access to CIOs is via respected networks and communities of interest. To help get CIOs involved with your board, consider three things they might be interested in: 1) Access to your leadership team, 2) Ability to help with your roadmap and be involved, 3) A good deal for the company they work at.


How a Startup Wins the Deal – 5 Important Steps

  • Step 1 – Define the current state of your customer’s network or application stack. Not being judgmental, just document it. Put it on paper.
  • Step 2 – Capture the issues and opportunities with the current state. It can’t just be filled with problems; you should include opportunities as well.
  • Step 3 – Propose a future state with your solution.
  • Step 4 – Solve the issues – Show how that future state is addressing each of those issues and opportunities that were called out in the current state. Don’t just trade one set of problems for another.
  • Step 5 – Show a roadmap on how to get there – the customer journey and how you make it happen.
  • Bonus point: What’s the ROI/payback?


Figure Out Your Industry Targets

Some people are taking 20-30% budget cuts. Don’t sell into them right now. It could be a good time to develop a relationship though.


Selling Inside vs Outside Silicon Valley

It’s good to get early wins with your friends inside Silicon Valley, but remember that things will be different outside in the larger world. It’s nothing like selling to a global Fortune 500 or 1000. Talk through with your sales team how IT orgs actually work, what are the drivers and where are the areas you can fit in. It’s not about the tech, features, or functions – you need to be able to tell a story (which will vary depending on audience, CIOs – more business / CTOs – more technical, some business / bank/build-shop CTOs – more technical).


Take a Portfolio Approach

Take a portfolio approach when dealing with clients – have a couple of large companies, but have a portfolio of smaller companies. The sales process, legal, procurement, etc. on large companies is very difficult.


Land & Expand

Don’t try to win an entire corporation – sell to a small part of the corporation and prove your value. If you succeed with one part, others will come to you over time. Make yourself visible to the rest of the businesses within the corporation (similar to getting corporate logos to be visible to other corporates).


Know When to Say “No”

You can’t pivot into things that aren’t replicable for other customers. You have to say, “No, that’s not on our roadmap.” Your BD and sales orgs have to have their motivations in the right place – not on a per deal/per transaction basis.


Promises Made & Promises Kept

Prove your value by keeping your promises. Do a great scope up front, figure out your customer’s KPIs and pain points, then try to meet and exceed those things fast – speed is important these days. Make the person on the buying side look good. Don’t over-promise and under-deliver.


Perfecting the art of the sales pitch is critical for startups, now more than ever. Thanks again to Alan, Brian and Mark for sharing their stories and best practices for selling to CXOs during these challenging times. These experts are part of an extensive Mayfield CXO Network of CIOs, CTOs, CISOs and leaders of innovation who are startup-savvy technology and business leaders.

For more expert insights on thriving in tough times, check out the previous posts in the series.

  • Originally published April 27, 2020