Sales Executive Corner

How Sales Leaders Go to Market and Win in the Most Uncertain Market Ever

Anna Baird, Chief Revenue Officer at Outreach's Avatar

Anna Baird, Chief Revenue Officer at Outreach


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Sales leaders face a crucial double-challenge: They must accelerate efforts to modernize their teams and systems with emerging digital technologies and tools — while keeping their salesforce motivated and engaged during a global pandemic.

In short, they need to pick up the pace with go-to-market strategy during one of the toughest markets ever.

Some tough questions go along with tackling those challenges:

  • How do you motivate your go-to-market team every day during a time of constant uncertainty?
  • In a critical business discipline that relies so much on interpersonal rapport, face-to-face meetings, and hands-on guidance of customers, how can your teams continue to build great relationships with remote tools and technologies?
  • Perhaps even more important: How do you ensure your sales team has the emotional and mental strength to power through?

That’s a challenge that the pandemic has made more urgent — not just for sales organizations, but for business at large. According to research by mental health company Ginger, 70 percent of U.S. employees today say that working through the pandemic has been the most stressful time of their careers.

In my experience, however — and in talking with other industry leaders — I think CROs can plot a smart path forward. Following are a handful of approaches to consider to set up your teams for long-term success, at a time when all of us can become preoccupied by short-term challenges.

Focus on the long game

Sales leaders need to plan for the long haul and to give up on the unrealistic notion of “returning to normal.” Instead, they should look at COVID challenges as an opportunity to get ahead. Case in point: As a McKinsey report notes, even though roughly 90 percent of sales today have shifted online in one way or another, more than half of companies today believe the sales methods they’ve been adopting on the fly since the pandemic hit are actually more effective than pre-COVID methods.

Sales leaders should step back from the uncertainty and focus on positivity. One helpful tactic to consider: Start forward-looking conversations with your sales teams about long-term messaging and objectives. Avoid focusing on current — and likely limited — budgets and resources. Lean into the most relevant challenge at hand: How can you help your customers prepare for an uncertain future? Finding innovative answers to that question will help lead your team.

Lean into digital to reach customers in new ways

I’ve worked with Fortune 50 companies in recent years that are still managing their sales organizations with spreadsheets. That approach isn’t just untenable logistically, it handicaps sales leaders from gleaning critical intelligence from the data.

So how do you gain greater visibility into critical sales and CRM analytics — and do so, if necessary, on a limited budget? Now is the time to pivot to technologies that can offer new direction and insights for your go-to-market team.

For example, it takes between five and 10 touches for a sales rep to connect with a new prospect, according to a 2018 study by the RAIN Group. I think that number will only keep rising as more inputs and content sources compete for customers’ attention. So how do you win that battle with technology? How can digital tools and workflows support your sales teams along this journey? How will you break through that noise?

One of the most effective strategies is to develop, target, and deliver high-quality digital content, so your sales teams can get the right messages to all the right personas — and at scale. Tap into sales engagement tools so you can pivot your go-to-market teams to where they need to be.


Clear away clutter to let your people focus on what matters

CROs need to give their teams the technologies they need to be more efficient — while finding ways to relieve the stress that everyone is struggling with.

Happy employees, after all, are the most productive and successful. One winning strategy to keep employees happy is to use automation tools to their advantage. In many organizations, sales personnel are overloaded with rote tasks that have little to do with serving customers: filling out paperwork or entering data by hand. Nearly two-thirds of sales reps’ time today is spent on non-revenue-generating activities, according to a recent survey of more than 700 sales reps.

Sales engagement tools can help offload the scut work and give your teams back precious time to engage with their clients, or to restore and replenish themselves. Making sure they can accomplish both is invaluable to long-term success. Positioning new sales tools as an employee benefit has proven to give sales teams a morale boost and generated better results. According to a 2020 Forrester report, 41 percent of B2B companies are reinventing cost savings into new sales technologies that can boost efficiencies and outcomes.

A customer with more than 20 years’ experience in the sales industry recently raved to my team, “Outreach has kept me more organized and productive than I’ve ever been!” Having access to the right technology has freed up his time to manage many prospects at one time and to focus on high-quality activities that improve overall customer satisfaction.

While I’ve emphasized that sales leaders should focus on the long term, it’s crucial to start making changes in your organizations today to achieve whatever is on your big horizon. Tap into digital technologies to give you the insights you need to motivate and monitor your go-to-market teams — before the market shifts again.

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