Sales Executive Corner

Leadership and Adaptability in a Remote Sales World

Anna Baird, Chief Revenue Officer at Outreach's Avatar

Anna Baird, Chief Revenue Officer at Outreach


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“It’ll be a few months of shutdown, then sales leaders will be out seeing customers again.”

“We’ll definitely be back to normal by fall — worst-case scenario, the new year.”

“I hate to say it, but the new year was too optimistic… this can’t go on forever, can it?”

We’ve watched a global health crisis, economic downturn, social inequalities, and polarizing politics upend the world over the past few months. The light at the end of the tunnel feels farther away every day.

And we no longer have the luxury to wait and see what comes next.

As a chief revenue officer with more than 300 go-to-market professionals looking to me for direction, I too hoped we would get back to normal — that our quarterly financials would look much stronger. But it’s clear that uncertainty has become the new normal. And no one is handing sales leaders “get out of jail free” cards. We must still hit aggressive sales goals and stay upbeat while evolving our sales strategies to function differently in a remote world.

In my role, I talk to peers and customers every day about how they’ve leaned into new ways of doing business. Here are some of the ways sales leaders are remaining adaptable and motivating their teams.


Control what you can control

Many companies are hesitant to make major decisions right now, and our front-line teams are feeling the brunt of this indecision.

Several executives have said to me, “I don't know what to say anymore. Everyone is looking to me for answers. I even have people asking me when the virus will go away!" Our teams expect us to know how to fix everything that’s broken. That’s not surprising: It is, and always has been, our responsibility as leaders to make sure our employees feel supported.

But how do we lead in the current climate?

The most effective way leaders can help is to own that circumstances aren’t changing anytime soon. Look challenges straight in the eye, and do what you need to take care of your team and your customers right here, right now — even if it’s way out of your comfort zone.

I’ve had to coach my teams to adjust their selling approach depending on who they’re talking to and how comfortable they are with imminent changes. They are meeting with people who are worried about getting laid off or, in some cases, already have been. It’s one thing to hear someone tell you no; it’s another for someone to be in tears on the other end of the phone.

“Control what you can control” has become our mantra.

So what can we control? Understanding our teams. We can check in regularly and engage in deep conversations. We can schedule all-hands team meetings and open up anonymous Q&A to make sure everyone feels comfortable asking tough questions.

We can also control who we sell to and how we sell to them. Technology gives us clear visibility into rep performance as well as insights into what’s broken — and what’s working — so we can focus every person on the team on the right areas.

Most sales leaders in the current landscape have had to pivot to new messaging and new markets to drive new vectors of growth. They’ve also had to lead with empathy and nuance as they managed underperformance. The best leaders congratulated teams for their winning mindset and motivated them to control what they could control — like driving additional opportunities with people who already love their product.

Keeping the customers you have should always be your top priority, no matter what’s going on in the world.

We’re analyzing if customers have the potential to transform more in the next six months. Is there even more they can do to prepare for the future? Growth-minded customers are your best avenue for expansion.

Pivoting quickly is crucial right now to maintain relationships with your best customers and help them bet big in this remote world.

Things felt out of control in March. But companies were still buying, so we had to reset and walk arm in arm with current customers as things changed daily, while learning new use cases to go after new opportunities.
In 40% of our top deals, customers doubled down — they expanded their Outreach investment in Q1 and then again in Q2. We also added more new logos in Q2 than in Q1.


Human connection matters more than ever

The sales reps who sharpen their active listening skills during every virtual meeting will reap extraordinary benefits in a remote selling structure. It may feel less natural, but deeply empathizing, responding, and gathering feedback is crucial to building relationships.

I watched one of our teams talk to a senior leader about the business challenges they need to solve. For 30 intense minutes, our salesperson asked deeper and deeper questions until the customer revealed pains they didn't even realize they had. By the time the quick call ended, we felt a level of connection that usually only comes after multiple in-person meetings and dinners.

As another customer told me, “It takes a lot of effort to read body language on Zoom. After personally hosting almost 1,000 video calls in the past five months, I’m blown away when people have the energy to track whether I’m engaged and make sure that I’ve understood their materials.”

Intentionality like this is mandatory when your view to the outside world becomes a 14-inch laptop screen. Similar to how we connect with movie characters on a screen, we need to pay attention to the details of our customers’ story and their business challenges.

Now is the time to master the basics of relationship building. Make sure to review recorded sales meetings to look for the bright spots. Did everyone introduce themselves and their roles? Did they have a chance to ask all of their questions? Did someone get interrupted when multiple people spoke at once? Did your team ask everyone (even the person who started last week and is still onboarding) to weigh in? Did they lean in when a customer talked?

This attention to detail carries over into how we connect with one another, especially since we’re not in person. Encourage your team to stand out by empathizing, listening, connecting, identifying pain points, and aligning solutions with business goals. And always compliment their efforts to master their craft.


Thinking critically and creatively about employee happiness

Great salespeople expect to win, and today’s selling climate isn’t doing their confidence any favors. Team leads are feeling it, too: It’s one thing to manage a “remote sales team.” It is an entirely different thing to manage a “stuck-at-home sales team" where a quarter of your team has never met their manager (or customers) in person.

I’m constantly trying to keep perspective as a leader so I stay laser-focused on the person on the Zoom screen in front of me. How can I help them feel better about the changes at large so they understand how it impacts their day-to-day jobs?

Like many other companies, we started hosting virtual lunches and events back in March. Some leaders have told me they don’t think any of this “works.” I agree that a Zoom happy hour does not make employees happy per se, so we’re leaning in on creative new ways to strengthen relationships despite the distance.

We are experimenting with things like weekly team prize wheels and group exercise breaks to encourage our people to get to know each other. Team-bonding activities also come with the added benefit of improving overall employee well-being, which Harvard Business Review affirms is the key to happy customers.

As we assess employee morale, our leaders are also taking a critical look at the processes we built before we moved our teams inside. Are we really structured to be the most successful in today’s environment? Do our teams have what they need to effectively do their jobs in this new setup? Although we’re not ready to make any major organizational changes, we know now is the time to plan for a long future of remote work for us and for our customers.

A part of that planning means we’ve invested in training our leaders to listen and support their teams in areas usually ignored in the workplace, such as racial and political issues. We’ve invited in experts to teach us how to build respectable dialogue around these topics during conversations with both customers and colleagues.

We’ve also hired coaches to help our team stay mentally "fit" and build resilience. Through weekly tips and meditation sessions, we’re helping our teams know they can (and really should) take the time and space to get mental breaks every day.

We are in a marathon full of sprints, and focusing on our people is the only way we’ll come out of all this stronger.


The adaptable sales organization

Our sales teams will never look the way they did before. While others are taking a fearful step back, sales leaders have a massive opportunity to help move business forward.

Leaders need to lean into discomfort and take control of the things they can now. Employees need to connect with coworkers and customers more than ever in this remote sales world. Companies need to invest in innovative ideas to support team building and morale. And we all need to take care of each other.

We know now that more changes are coming. Adapting quickly has become the “new normal.”

Ready to learn more about how industry leaders are adapting to the new way of selling? Join us in September for The Adaptable Sales Org.