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Selling in a Crisis: Insights from Leaders Who Have Done it Before


“The pessimist complains about the wind. The optimist expects it to change. The leader adjusts the sails.”

I think John Maxwell, author of one of my favourite quotes, would agree that the winds are blowing pretty hard at the moment. As salespeople, we’re used to facing many challenges — from listening to prospects and customers to understand latent needs, to engaging prospects with compelling storytelling and overcoming objections of every sort to deliver results each quarter. But the COVID-19 crisis has upended all expectations for the year ahead. Now, the table stakes are simply to survive.

Even as we face daunting obstacles, remember that every crisis is an opportunity to accelerate change and build a stronger team in the process. With the needs of your sales team in mind, it was my pleasure to host a discussion with two experienced leaders: three-time entrepreneur, CEO, and author Bob Tinker, and Portag3 Ventures Senior Sales Principal Brendan Callaghan. Together, we shared insights on understanding customer psychology, adjusting your go-to-market playbook, and leading with empathy and decisiveness during this difficult time. Our key takeaways are summarized below.

“Suddenly, you’re no longer a rag-tag bunch of frontier people. You’re a highly organized, well-oiled army charging across the plains. As Bob puts it: you’re in Braveheart mode.”

Preventing Churn and Protecting Existing Revenue

As a sales leader, your number one priority during this crisis should be to prevent churn and protect Annual Recurring Revenue (ARR). Start with the customer and work backward to identify and prioritize actions. Reach out to your existing customers to gauge their situation and find out how you can help them navigate new problems. Remember that every single one of your customers has their own set of executives breathing down their necks to cut costs. Make sure you’re top of mind and reinforcing your value to be part of the solution.

As you ramp up dialogue with current customers, do not assume that a recent deal with a new customer means a long-term relationship is “in the bag.” Your relationships with new customers are at high risk of churn until you have fully operationalized and made your product mission-critical for their success. Follow up and make yourself integral to their business.

Requalifying Your Sales Pipeline

An important goal in your customer conversations is to requalify your existing sales pipeline to reflect their new needs. Many of your competitors will simply dress up their existing value proposition with “COVID-friendly” language. This marketing exercise is already tired and ultimately ineffective. Take a look at your customer segments and ask, which segments are high-risk and should take priority? Are there other industries (or verticals) worth pursuing? Reach out to twenty new prospects and talk to them about their pain points.

Different industries are not the only places to find new leads. In your ecosystem of customers and prospects, identify different buyer personas. Review your past deal portfolios. Was it the CFO that signed off on the sale? Was it the IT department? Keep in mind that there are many buyer personas within an organization, and your value proposition will be slightly different for every single one of them. Test your success with each different persona, and adjust your playbook based on what works.

Unlearning Old Habits and Re-Finding Your Urgency

To quote Bob Tinker’s vivid metaphor, in the early stages of building a company, you’re in “Davy Crockett” mode. Like backwoods explorers, you and your team are finding your way through the woods through experimentation and iteration, without a roadmap. It’s a messy affair until, by trial and error, you build your Go-To-Market Playbook — a repeatable, scalable process to unlock your business’s growth. Suddenly, you’re no longer a rag-tag bunch of frontier people. You’re a highly organized, well-oiled army charging across the plains. As Bob puts it: you’re in Braveheart mode.

The COVID-19 crisis likely requires us to step back into Davy Crockett mode. Large organizations naturally have muscle memory — a set of reflexes to the problems they’ve faced in the past and the solutions they’ve found over time. But as of four weeks ago, those problems are different, and so are the solutions. Instead of scale and optimization, you must focus on survival. Instead of charging ahead with your existing value proposition, you must adjust your value proposition, messaging, positioning, and likely your product as well. It’s imperative to emphasize benefits over features, direct and immediate cost savings over indirect benefits, and — above all — simplicity.

Learning how to “unlearn” is more than just a coping mechanism for the current crisis. It’s an essential skill for building a company that can move beyond the first few successful sales and unlock scalable growth. This crisis is an opportunity to re-discover urgency — that special thing that will compel customers to buy your product. Before the 2008 recession, Bob’s startup MobileIron was focused on providing security and productivity gains to customers. When the economy crashed, productivity was no longer a primary selling point. Customers needed — urgently — to save money.

With this in mind, Bob’s team discovered a way to deliver just that: a part of the product that helped customers detect international roaming and avoid costly charges. That function clinched their success. MobileIron went on to close Series B funding and went public in 2014.

Refocusing can be painful. It can feel like a betrayal of your founding vision. But it isn’t. Remember, start at the customer’s needs and work backward. Find out what is urgent to them. There are things that are interesting — and then there are things that are urgent. Sniff out that urgency.

Leading with Empathy and Decisiveness

From the moment this crisis began, the pressure has been on for managers to show decisive leadership. To inspire confidence in your team, articulate a clear and compelling plan. Paint a picture for them. What were the old goals, and what are the new ones? What has changed, and why? How will everyone be affected? Be a beacon of calm and confidence. Show extra gratitude to your team, your customers, and your partners. Reassure your team by giving them the facts, and they will be able to focus on the challenges ahead.

Making cuts to your team is one of the most gut-wrenching decisions a leader will ever have to make. As much as you can, be clinical in your analysis and decision-making. Remember, you can’t be there for your employees if you do not survive. Find the new metrics, but balance those metrics against empathy. Your decisiveness, as well as your compassion, will be remembered. Finessing this duality is important, yet exceptionally difficult for most leaders.

As leaders, we all have the tendency to put everything on our own shoulders. But no one can do it alone; navigating a crisis is a team sport. Sit down with your team and open up a dialogue. Seek feedback and co-author your new plan with them; aim for “build-in,” not “buy-in.” Your team is closest to the customer and is eager to help carve a new path. Finding the humility to truly collaborate can lead to powerful experiences and forge enduring relationships, both professionally and personally.

How you respond to this crisis will depend on your mentality. Ask yourself: are you a player, or are you a victim? Are you above the line or below the line? Your response to this question is a choice. If you decide that throwing in the towel and giving up isn’t an option, then it won’t be. Get up after each setback, dust yourself off, and keep moving forward.

While the next few months promise anything but smooth sailing, you can steer your way through these perilous straits by responding to your customers’ shifting needs and re-finding your urgency. With a little adjustment, you will harness a spectacular opportunity to accelerate change and emerge from this crisis with the wind at your back.

Key Takeaways on Selling through the COVID Crisis

  • Increase communication with customers to understand their new needs and to prevent churn and protect ARR.
  • Leverage insights to re-discover your urgency and help customers do more with less.
  • Unlearn old unproductive habits and re-build your go-to-market playbook if need be.
  • Lead with empathy but exercise decisiveness.
  • Collaborate with your team members. Crisis management is a team sport requiring more “build-in” than “buy-in.”

We empower and invest in visionary financial entrepreneurs. Learn more about Portag3 Ventures at

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