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CxO Corner: Perfecting The Approach To Selling During A Crisis

Here at Work-Bench, we understand that getting in front of CxOs is tough and standing out from the crowd during COVID-19 can be even more difficult. Early-stage startups have a lot on the line, so nailing their messaging and approach while selling to new and existing customers is critical as doing so incorrectly can ruin their chances at a sale and damage their reputation.

This is a two part edition of CxO Corner, our Q&A series with our Fortune 500 executive network. Our first post dove into the Shifting Priorities for Enterprise Leaders During COVID-19 and in this post, we asked our executive network to share the effective measures they’ve seen vendors take to help get their product on the map during this crisis. We hope these suggestions can help guide you on what methods and strategies work to get CxOs’ attention.

Don’t Make It All About COVID-19 & Get To The Meat

Nothing is more insensitive than ambulance chasing during a crisis. “For new engagements, I get annoyed when I see COVID-19 as their opener,” said the Head of Infrastructure at a global financial data company. “Companies shouldn’t necessarily focus on COVID-19, but should be focused on technology, unique opportunity, and community.”

He shared a good example of how to approach edge computing: “Educate me on what the architecture looked like before and what it should look like now. I would like to understand how if you have, for example, this software agent that installs on X and Y that it will provide Z benefit, such as better telemetry, monitoring, or performance.”

Determining your unique value set and explaining it succinctly upfront is important. You’ll be able to do this best by listening to the customer to understand their immediate and likely shifting problems. “Don’t make assumptions,” said the CTO at a large US-based investment management firm. “Look and ask for deficiencies in current product sets and explain how you may be able to help bridge that gap.” He also added that consumer-like experiences are powerful in the enterprise and that information workers now “expect technology to operate at work the same way they do in their personal lives.”

Creating easily digestible and easily accessible content, such as short videos and whitepapers is a great way to provide CxOs with clear information about your company and product. Partha Chakraborty, Former Director at BMO Financial Group, mentioned that “A very short video (less than 3–5 minutes) on their capability in handling current workforce challenges will be the best way to grab executive attention, as opposed to bombarding 1–1 emails, which might not get any response.”

Reducing the time to understand what you do better serves your potential customers, as well as helps you make the most out of the time you will spend with that client since they already have the background and are actually considering engaging with you.

Flaunt Your Case Studies & Shorten Evaluation Time

While organizations will vary in size and complexity, enterprises will look at how you work with industry peers to see if you can already satisfy the requirements of a company similar to theirs. Having specific examples of how you work with other organizations in the same industry can also showcase tangible benefits that they can expect to achieve.

“Most startups and vendors are promoting their products through technical capabilities,” said the Head of Infrastructure Architecture and Security at a major global bank. “But I think what’s more interesting is their user stories — how other companies are using their products and what the benefits were. This is especially important for banks, as we are heavily regulated and knowing that other banks were able to implement the solution/product, means that there is a way to go over the regulatory hurdles. It also helps to think of new use cases that were not in our mind. Some startups/vendors do that, but it’s clearly not the norm.”

When time is of the essence, simplify the evaluation, adoption, and deployment cycle. The Head of Technology at a global investment manager finds that this is best done by “concentrating on verticals and building out complete MVP service offerings, along with anticipating and building in security and identity features that large enterprises require.” He doubled down on the importance of quick technology adoption, stating startups should, “price for the long-term as tools that ramp up too fast in costs will be frowned upon in today’s economic environment.”

Much like my colleague Jon Lehr mentioned in his blog post about giving your buyer superpowers, the same Head of Technology also finds it beneficial when companies “Provide examples of ROI and TCO to help build business cases.” The more work you can do for the customer to arm them with information on value, the easier a decision can be made. Even better, “making these available as spreadsheets allows customers to extend contracts as needed.”

Add a Human Touch

Especially in challenging times like these, it’s important to build lasting goodwill with your customers. Brian Poppe, SVP at Mutual of Omaha values personal relationships. He shared that “The ‘customers’ seem like large, faceless entities. Recognizing that there are actual people behind those names and building on those human connections forged before the pandemic will be the best, most effective way to work with your customers and prospects. We’re all struggling with the lack of connection, so a simple ‘Hello, how are you?’ without a sales motive will result in a stronger long-term relationship than trying to reposition your product/service to serve differently.”

Similarly, the Head of Technology at a global investment manager believes in “adopting a client-first attitude always makes the difference between a great partner and one you tolerate.”

These are a few of the playbook pages from our CxO community. If you’re a CxO and would like to share insights or advice on how startups can best work with enterprises during this time, please reach out!




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:

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