How I create an effective sales strategy as an Outreach sales leader

Posted August 9, 2023

Shay Keeler headshot

By Shay Keeler

Senior Director of Sales at Outreach

Sales leaders are under more pressure than ever. Not only are we expected to hit sales targets amid a tough economic climate, we’re also called on to run a predictable revenue organization in a time of great uncertainty. 

What’s more, burnout among sales teams is high—89% of B2B sellers recently surveyed by Gartner reported feeling burnt out from work, citing a disconnect from leadership as a major reason. 

So what’s a sales leader to do? Build an effective sales strategy. 

It may seem like a shockingly simple — and obvious — suggestion for a complex problem, but the truth is, too many of today’s sales leaders are trying to tread water without any kind of sales strategy in place. With the right one, it’s possible to predictably create and close more pipeline — and empower sales teams in the process. Here, I’ll walk you through my approach: 

  1. Execute a successful sales strategy
  2. Set goals and measure results
  3. Help my sales teams create qualified opportunities and turn them into closed deals

Step 1: Figure out where you’re starting from

Every sales strategy needs a solid starting point. In other words, you need to identify how and where your current sales strategy is preventing you from achieving your goals. 

Maybe your deals are getting lost in a sea of stakeholder approvals. Maybe your reps aren’t reaching out to the right prospects. Maybe your sales enablement materials aren’t a good fit for the specific buyers you’re going after. To identify these gaps accurately, you need to ask the right questions.

I recommend asking the following questions to get a good feel for where you’re starting from:

  • What parts of the sales funnel seem to be working well, or not working at all? 
  • Are you getting enough opportunities but not able to close enough deals?
  • Are you not getting the right personas in the room to close the deals?
  • Is prospecting the issue? 
  • Is there a disconnect between sales and marketing? 
  • Do your sellers know how to talk about the product? 

Once you’ve answered these questions honestly and with as much detail as possible, it’s time to group your answers by focus and priority. The key to an effective sales strategy is consistency, and clearly organizing and ranking your problems will help you build a strategy that’s consistent in its focus and tactics. Ultimately, this step will help you build the foundation for a healthier sales process.

Step 2: Set the right goals

The right sales strategy will help your team do two things: create and close pipeline. The goals you set as a sales leader should do the same. 

In Step 1, you laid the groundwork necessary to understand where your team is starting from. You also organized and prioritized each of your problems. Now it’s time to use that list of prioritized problems to set goals. 

The goals you set for your team should be specific and tactical and eliminate ambiguity.

Be specific and tactical

Your list of goals should be as specific as the list of problems you created in Step 1. It’s not enough to tell your team to “do more.” Each goal should be tied to a priority that will either help to create or close more pipeline. 

Your goals also need to be tactical. For example, do you know exactly how many people need to be put into a sequence to get to your pipeline number? You should. When you do, it’s easy to hold your team accountable with crystal-clear expectations they can tie to their own performance.

Eliminate ambiguity

It’s one thing to give your teams specific goals, and it’s another to show them how to achieve them. You can’t give your reps a number to hit and then expect them to figure it out for themselves. 

Coach your reps on how they’ll reach the goals you’ve set for them. This requires specific, frequent feedback and conversations. You should be able to coach your reps through which motions can help them both create and close more pipeline.

Step 3: Create more pipeline

Understanding where your sales team is starting from and which goals they should be achieving is a great start to building an effective sales strategy. Now it’s time to put that strategy into practice by creating more pipeline. 

When your team creates more qualified leads, they’re less likely to lose them later on in the sales cycle. 

The golden rules of creating pipeline

  • Be exceedingly clear with expectations. For your team to create qualified pipeline leads, they need clear expectations to operate within. This should be easy when you’ve set and communicated clear, action-based goals. For example, we use the sales methodology MEDDPICC along with Outreach to qualify every deal in an efficient, consistent way. 
  • Be relentless with accountability. Get comfortable with uncomfortable conversations. Ask people how they want to receive feedback about their performance, and stick with that. That might feel like micromanaging — it’s not. It’s your job as a sales leader to hold people accountable to their numbers and to help them improve if they are falling behind.
  • Know the difference between “skill versus will.” When your team is falling short on booking meetings, it’s your job to recognize that and identify why. In other words, is it a skill issue where you can coach and develop them further? For example, if I find out one of my new sellers is struggling because they don’t know how to use Outreach to prospect efficiently, that tells me that better onboarding might be what they need. Getting to the root of the problem will help you solve it more quickly and effectively.

Get a unified view of prospecting efforts

Driving an effective sales strategy means keeping a close eye on prospecting efforts to amplify what works and iterate on what doesn’t. Using a tool like Outreach’s Sales Execution Report helps you do exactly that. 

Using a report like this helps me assess all prospecting efforts in one single view, so I can understand team performance for any given timeframe.

The Sales Execution Report brings all the important prospecting metrics into a single view so you can understand overall performance, team performance, or user performance for specific timeframes.

Step 4: Close more deals 

The final stretch of a solid sales strategy? Closing more deals. Coaching your team to do this requires a different set of problem-solving skills than creating pipeline. Here’s how you can help.

Be proactive, not reactive 

Don’t wait for problems to surface to solve them. I use Outreach’s conversation intelligence solution to search recorded meetings by topic, call trends, or call insights, allowing me to intervene early if a deal is going south. For example, a major indicator of whether a deal is going to close is discussing next steps. When you listen to your team’s calls, are they touching on next steps in the last five minutes? If not, coach them toward that. I also look at mutual action plans in Outreach to monitor deal progress. Lastly, deal health insights in Outreach let me quickly see where my sellers’ deals have risks, and help me coach them with the right actions to take to get back on track. 

Mutual action plans in Outreach help sellers align and collaborate with their buyers to drive smooth, predictable purchase processes.

Make the first half hour of the day the most productive 

I spend the first half hour of every morning going through all of my team’s existing opportunities in Outreach and identifying next steps (or creating them if they don’t exist yet). With the deal grid in Outreach, I can investigate if my team has enough early-stage pipeline, if I have deals that are stalled in the middle, and other key details to continue tracking. Setting aside this time to make a clear plan for the rest of the day sets the tone and ensures nothing falls by the wayside.

See an overview of the activities an AE is taking within the deal to progress it toward close, such as number of meetings booked or emails sent.

Leverage an AI-powered platform 

Your sales strategy is only as good as the sales tech stack that you’re leveraging. To ensure that every action your team takes is consistently building pipeline without sacrificing deal velocity or pipeline conversion rates, you need a single source of truth. Investing in an AI-powered sales execution platform gives you a complete picture of the entire sales cycle so you can effectively implement your sales strategy to create and close more pipeline. 

Interested in learning more about the latest capabilities from Outreach? Learn how to leverage Outreach as the only complete platform for all selling activities this October in Seattle. Visit the Unleash 2023 event page to see the full agenda, keynote speakers, and special events!


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