Subconsciously, I’ve been preparing for my role at Outreach for my entire life.

Back when I was a sales leader, I loved training. It was super rewarding to watch someone learn a new skill, apply it in the real world, and reap the rewards. It was a part of my job that didn’t feel like work.

I loved training so much that I sidestepped out of sales management and into sales enablement. I honed my skills in a handful of roles, learning how to build impactful and scalable onboarding and training programs.

After 10 years in the industry, the opportunity every enablement professional dreams of appeared on my radar: Sales Engagement Platform, Outreach, was looking for a senior enablement leader. The role was helping sales reps sell sales software to other salespeople.

It felt like the pinnacle of my career. I accepted their offer and moved across the country to meet my new team. 

Ride the rocketship

There’s a popular idiom in Silicon Valley: “You’ve got to build the plane while you’re flying.” In other words, you’re building the company while it’s operating and growing. But a plane doesn’t do justice to the circumstances here. Outreach felt like a rocketship. It was scaling so quickly that people were just trying to hold it together while building new components to keep up with the rapid pace of innovation.

To make matters even more challenging, the company had gone without an enablement leader for around 18 months. (Although, I will say my predecessors had cultivated a strong learning culture. I inherited a team that already craved enablement, which is often one of the toughest challenges.)

While the existing enablement team was working hard, they didn’t have anyone setting the direction or driving things forward. For example, employee onboarding had shrunk to keep up with the rate of hiring. Sales technology adoption was low, too. Cross-functional collaboration was another casualty. 

Suffice to say, there was quite a bit of enablement debt.

Rebuilding the launchpad

I spent my first six months rebuilding the enablement foundations—the launchpad, if you will.

I began with our technology. Adoption among reps had slipped over the years, which in hindsight was entirely understandable. Outreach had doubled its revenue every year since 2014 and its reps were working flat out to keep up. It wasn’t as if they could hit pause on their sales and spend a week relearning our enablement tools.

But this provided an opportunity. Instead of rebuilding trust, interest, and engagement in the old, unused tool, I saw this as a chance to introduce something new and update our tech stack. And that’s precisely what I did. Although it caused some minor disruption to the reps using the old technology, it was easier to generate widespread enthusiasm around a brand new launch.

Instead of rebuilding trust, interest, and engagement in the old, unused tool, I saw this as a chance to introduce something new and update our tech stack. And that’s precisely what I did.

My second significant project was to kickstart cross-functional cooperation. I drove a shift from enablement owning only deliverables to our team owning outcomes. For example, we no longer own onboarding because it’s a complex process with dozens of different stakeholders involved in the process. But we own the strategy. We guide onboarding design to increase engagement, boost learning, and decrease ramp time.

It felt like we accomplished two years’ worth of work in just six months. But fixing the launchpad was just the beginning. I was gearing up to transform the entire enablement function.

Go for liftoff

Enablement professionals are often incredibly organized and detail-oriented. They seek out information from a variety of different sources. They build engaging learning tracks. They use work back schedules to work out what content to share and when.

In an ideal world, that works perfectly. But the reality is often imperfect and non-linear.

Consider a rep moving through a typical onboarding process. After a couple of weeks of basics, their trainer moves on to specific process work like building quotes. But here’s the problem: That rep won’t have to build a quote until months later when they’re actually doing their job. By that point, they’ll have forgotten how to put everything together. To relearn the process, they’ll have to join a new cohort’s onboarding session or we’ll have to carve out separate time for one-to-one learning. Both options are highly inefficient.

This problem plagues enablement professionals all across the world. Or, at least, it did.

It feels like we’re at the start of a new era of learning and development. One of the tools I introduced was a digital enablement platform called Spekit. With Spekit, we’re equipping sales enablement to cope with different learning styles and competing factors people have in their life. This allows us to embed training content within the tool a rep is using, empowering them to learn on their own.

With Spekit, we’re equipping sales enablement to cope with different learning styles and competing factors people have in their life. This allows us to embed training content within the tool a rep is using, empowering them to learn on their own.

Think back to the rep who was struggling to build a quote. Instead of waiting for a training session, they can now access the training content directly from Salesforce and relearn it on their own and in their moment of need.

After I got the launchpad to a point where I was happy with it, I refocused on Spekit. I partnered with revenue operations to craft our most important training content and workflows in the platform and rolled it out to our sales reps. We used Spekit for new use cases—new stages, new pricing, and packaging processes—which helped our training investments make it onto the front line.

Using Spekit means we can now deliver information right when the rep needs it, reducing retraining requirements and driving a much higher return-on-effort from my enablement team.

Using Spekit means we can now deliver information right when the rep needs it, reducing retraining requirements and driving a much higher return-on-effort from my enablement team.

Standardizing our training process

We have an incredibly robust tech stack, but I’m embarrassed to say that we train on each piece of technology very differently. That creates a really inconsistent experience for the learner. After seeing the success of Spekit in supporting our enablement initiatives, I’m hopeful we can roll it out across the company to make learning consistent and concise.

I don’t see enablement owning this entirely. Other owners can pick up the tool and use it on their own. They can produce content, training, and enablement in a way that’s comfortable for them. For example, a rev ops leader could enact their quoting process change without relying on me or my team. They can feel more comfortable doing that themselves because we’re no longer this blocker.

Augmenting sales enablement with Spekit was like a proof of concept. Now, I’m hugely excited to see what the whole company can do with it.

Augmenting sales enablement with Spekit was like a proof of concept. Now, I’m hugely excited to see what the whole company can do with it.