Episode TwoHundredTwentyNine

What Makes an Effective Sales Development Leader

Guest: Stratford Canning, Director of Sales Development at Forrestery

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About This Episode

For someone so successful to admit to making leadership mistakes — that’s powerful.

Our recent guest on Sales Engagement had the courage and humility to share lessons he’s learned in sales leadership by explaining what he wished he’d done as a new leader.

I was blown away by hearing from Stratford Canning, Director, Sales Development at Forrester, about how sales leaders can learn from his experience.

“Before I knew it, I was an SDR manager, but I had very little experience of management of how to make those decisions and the challenges that are faced with sales development,” Stratford said.

The first thing we discussed was Stratford’s co-founding of SDL (Sales Development Leaders), and how that group grew out of changes he’s seen in sales development over the years.

What’s changed in sales development

The SDL group grew out of connections amongst the cofounders through the Revenue Collective.

From 4 guys meeting in the local pub, SDL has grown to 200+ active members in their Slack community. “I’ve been leveraging it for all sorts of things, whether that’s dealing with specific problems with the team and developing the team, or whether it’s implementing new ideas,” he said.

It’s been an ideal site to work through the substantial evolution Stratford has witnessed in sales development over the past few years.

More strategic

Gone are the days when you rely on email scripts alone to reach your Tier I accounts. “The way in which we prospect has now become a lot more strategic, thoughtful, and creative as well, which also makes it a lot more fun,” he said.

More technological

The software options available for sales are mind-boggling, not to mention the sophistication of analytics and forecasting.

More targeted, a.k.a. smarter

Working smarter means being more thoughtful in prospecting.

It also means:

  • Alignment with sales teams
  • Spending more time on research
  • Less activity but of higher quality

Organizations are buying differently now, and only those who are smart and strategic with an in-depth understanding of those businesses will be able to target specifically enough to appeal.

“Always be testing new approaches, making sure we’re staying creative and on our toes, instead of just defaulting to what we’ve used in the past,” Stratford said.

What makes an effective leader


“That’s the job of a leader — to make sure that balance is there and in the right places,” Stratford explained.

When you’re trying to coach a team full of people with plenty of experience, as well as those who are in their first job out of college, that’s a challenge.

When Stratford moved into leadership, he was an SDR with sales experience but no leadership experience.

His first phase in management was very tactical, being in the trenches and examining email templates. 

Only a few years later was he able to take a longer view and become more strategic about the sales role.

“There’s definitely a shift in someone’s sales in leadership, where they go from being in the trenches to taking that step back and looking at the bigger picture,” he said.

Stratford credited support from sales ops, marketing, and other sales leaders that gave him the “lightbulb moment” and helped him shift his own leadership perspective.

3 leadership mistakes to avoid

Stratford shared technology-related mistakes that he made as a newly strategic leader.

Mistake #1: Falling for exciting-sounding technology

Technology definitely helped Stratford think futuristically about his teams. But he admitted to being distracted by the excitement of too much technology.

“My first instinct was, ‘Great, I need all of that, that all sounds amazing,’” he said.

But some of the technology didn’t turn out to be effective in the long run.

Mistake #2: Implementing technology too quickly

This mistake isn’t quite the same as the first one.

It took the huge internal change caused by GDPR to force Stratford to slow down in terms of technology integration. 

“As a result, the technology that we have implemented has been far more effective, because we’ve spent a lot longer in evaluating and understanding how it should be adopted,” he said.

An implementation done incorrectly often causes more work down the line than not having the technology at all.

Mistake #3: Onboarding users too late

Getting your team involved early in the process (especially the veteran sales team members) will give you a better picture of how the tech can enable your team.

“My number one tip would be to make sure the team, the people on the ground, are involved in that process as much as possible — even if it means that process then takes a little bit longer,” Stratford said.

Don’t overlook how the new tech affects other teams in your organization, too. Get them involved and make sure their voices are also heard.

Bonus tip: Stay connected

A parting piece of advice that Stratford shared was to understand the challenges facing your team.

“Try and stay connected with your team,” he said. “Make sure you’re hearing them on a daily basis. Always keeping a link to your team is really important.”

For more engaging sales conversations, subscribe to The Sales Engagement Podcast on Apple Podcasts, on Spotify, or on our website.

About The Podcast

The Sales Engagement podcast is the #1 podcast focused on engaging your customers and prospects in the modern sales era. This show features real-life stories and best practices from revenue leaders doing the job day in and day out, in a casual, radio-like talk show.

Each episode features modern tactics, strategies, hacks, and tips to get the most out of your sales engagement strategy and help you navigate the next generation of sales. You’ll find energetic talks that will provide you with real actionable value around building meaningful connections and creating a better selling experience through authentic conversations that you can measure.

The Sales Engagement podcast is here to help B2B sales leaders, customer success leaders, and marketing leaders innovate and usher in the next era of modern sales by building pipeline, up-selling customers, and ultimately generating more revenue with more efficiency.

Hosted by Joe Vignolo, Senior Content Managing Editor at Outreach, and Mark Kosoglow, Vice President of Sales at Outreach.

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