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LEARN Recap: Creating a Winning Workplace Culture

Do you ever wish you could sit down with a successful CEO and learn more about how he created his own category, pivoted, and kept his focus through it all?

Our LEARN Spring keynote session with Manny Medina, CEO and Co-Founder, Outreach, allowed us to do just that.

Manny talked to WorkRamp’s CEO and Co-Founder, Ted Blosser, about category creation, what you learn from the ups and downs of building a successful business, technical and operational debt, and more. 

Outreach was founded under unusual circumstances. In 2014, the founders were in dire need of hitting a sales goal, so they built software that multiplied the effectiveness of their sales reps. That software became the focus of the company.

Outreach’s mission is to empower every sales rep and manager to achieve their full potential. The company offers a single sales execution platform where they can develop and close the pipeline with full visibility into the entire process.

Creating a new category in the market

Manny shares that creating a new category is a long process that isn’t for everyone. 

You have to name a category, but it doesn’t become official until someone else uses that category to describe you, so it takes a lot of patience and may never take off. 

Initially, Outreach named its category “sales acceleration,” part of sales enablement. They couldn’t get the official industry changemakers to accept sales acceleration as its own category, so they turned to their customers instead, educating customers and showing how sales acceleration could solve key problems.

Over time, Outreach created a category called “sales engagement.” After two years, Forrester created some movement around it. Outreach captured the category and continued to grow, but Manny realized that the company was missing the opportunity to help sales reps with engagement and closing deals. 

The team went back to the drawing board and re-defined its market segment as “sales execution,” which includes sales engagement but brings in the idea of an end-to-end solution. 

The key, Manny says, is to commit fully to the category. As he shares, “You can’t tiptoe your way into some of these decisions because you have to define the entirety of the company’s messaging, your packaging, your pricing, how you talk about it, how your reps are talking about it, your marketing material, your enablement material, your training. So you have to decide what you are going to be.”

Learning from the experience of founding a company

Next, Ted asked what one or two significant learnings Manny had throughout his tenure at Outreach. 

Were there things he’d do differently or things he would repeat? Manny shares two key takeaways from his experience. 

Managing operational debt

Operational debt is similar to technical debt. It builds up because you’re growing quickly but imperfectly, and then you have to go back and evaluate where you are and fix some of the flaws you let slide. 

However, many companies don’t address operational debt—people in roles that aren’t necessary, company departments that could be rearranged, and more—because it’s easy to overlook. It’s also hard to address from a personal perspective since these people have been with you for a long time. 

Manny advises teams to avoid just throwing more people at a problem. Instead, find ways the solution can be baked into your product or service. 

For example, onboarding was a challenge early on at Outreach, but they found ways to build onboarding practices into the software instead of hiring more people to onboard new customers. 

To address operational debt, consider taking the same approach companies do to tech debt—assign 20 percent of your resources to look at yourself, see what structure is in place, and determine if it’s necessary moving forward. 

Take the time to rethink the company, make decisions, and roll them out—not just bottom-up but also top-down. 

Solve multiple problems with one product

Manny shared that he’s recently learned you don’t need to follow conventional wisdom and build multiple products—instead, find ways to have your product solve multiple problems. 

“And then you realize that you don’t build multiple products, you solve multiple problems, and the product is a vehicle to solve those problems,” Manny shares. “So the way that you build your platform is you go back to the customer and say, if I were to solve more problems for you, what would that look like?”

This is especially important in Outreach’s target market, where sales reps don’t want or need a bloated tech stack. Instead, a single tool that solves multiple problems has much more value.

Manny shares he was bothered by the idea that 20 percent of sales reps deliver 80 percent of results. So his Co-Founder took a year to do a deep dive into why that was, getting past the platitudes and into the real reasons. 

The solution? Successful reps treat the sales process like a project and use project management approaches to make revenue more predictable. The AEs spent time in the middle of the funnel getting the buying group aligned to move the project (the sale) forward. 

That approach became a solution that Outreach could build into its platform to help all sales reps improve their success.

Read more: 6 Skill Development Tactics for Successful Teams

Managing productivity

Outreach has a unique view on productivity. Manny shares that the company looks at the primary goal they’re going after and then makes sure everyone is aligned with that and empowered to deliver on that goal. 

Once you’ve defined productivity for a group or department, you make sure each employee is equipped to come in, learn quickly, and then begin to execute the vision. This means ensuring clear direction, structure, and accountability at each level. 

“We have a cultural value called having each other’s backs,” Manny shares. “So having each other’s backs is making sure I’m delivering on my promise or my commitment to make sure that you are well equipped to deliver your promise or your commitment. And I’m not letting anybody down.”

This applies to any department—the focus is to create an environment where everyone is measured on the right output metrics, and the company can win together. 

Read more: 3 Ways to Create a High-Performance Culture at Work

Do-or-die projects

How does a company continue to grow and not get stuck in a rut, doing what they’ve always done? 

At Outreach, the solution is to have three “do-or-die” projects at any given time.

Manny points out that many expansion ideas are laid out as though a department can simply “go do it,” when in reality, the shift requires the entire company. 

For example, you can’t just go capture enterprise-level clients. You need to build solutions and messaging that those clients will be interested in based on their specific needs, which differ from other market levels.

So while most of the company is focused on the existing “train tracks” and ensuring everything runs smoothly and on time, specific teams are tasked with “do-or-die” growth projects. 

These become the focal point for the next big push in the organization. Once it succeeds, it graduates to a standard business operation, and a new do-or-die project begins. 

Read more: How to Future-Proof Your Organization

A culture that helps you win

Many people think of company culture as what makes it fun to work there or the relationships people have with each other.

Outreach takes a different approach. The focus of culture is to create the mindsets that help you solve target problems for your customers so you can grow.

“The culture that we’re working toward right now is an active culture,” Manny says. “So when you talk about trust, it’s not a trust like, oh, I can trust you. No, trust is the ability for you to move faster because you’re trusting somebody else to have your back. You trust the system, you trust each other, and you trust your organization. So we’re revamping our culture of values to talk about this move forward ability, this actionable energy that will allow us to get faster to get to our target.”

It’s interesting to think about company culture this way: a set of evolving values that focuses on helping everyone in the organization move forward, achieve their goals, and help the company win in the marketplace.

AI in the sales process

AI is undoubtedly a hot topic, so Ted asked Manny how he sees AI evolving in sales. 

Manny points out the importance of having feedback loops from monitoring and analyzing the data created by interactions between sales and leads. This information drives the AI models at Outreach. 

Also, generative AI is very exciting to the team at Outreach. As Manny points out, editing generated text is easier than thinking of messaging from scratch. 

He’s excited to infuse that into the organization’s workflow, simplifying the sales cycle for reps. 

But, he shares, “I feel like we’re just getting started. There’s just a lot more to come in terms of what’s possible.”

Watch on-demand replays from WorkRamp LEARN Spring 2023 for more actionable tips and expert insights.


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Anna Spooner

WorkRamp Contributor

Anna Spooner is a digital strategist and marketer with over 11 years of experience. She writes content for various industries, including SaaS, medical and personal insurance, healthcare, education, marketing, and business. She enjoys the process of putting words around a company’s vision and is an expert at making complex ideas approachable and encouraging an audience to take action. 

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