Katie MacDonald on Scaling and Iterating Optimizely’s Sales Enablement Program

Katie MacDonald is the Sr. Manager, Strategic Enablement at Optimizely, the leading platform for experimentation and A/B testing with over 250 million dollars in funding. MacDonald also has a wealth of experience from other companies with powerhouse sales teams like Salesforce and Savo.

On how a recession led her to her passion for sales…

I’m actually a certified high school teacher. I graduated college in 2008 in the peak of the recession so there weren’t very many teaching jobs available. However, people were always hiring for young, hungry sales people, so my first job was an SDR at Savo.

On the importance of deeply understanding sales functions as an enablement leader…

I moved up the ranks, hustling as an SDR, which I think was some of the best experience I could have asked for. As someone who’s now in enablement, it’s critical that I understand the grind it takes to build a healthy pipeline and the mental toughness it takes to make dial after dial. Eventually, I was able to make the transition to an Account Executive, and eventually to a Sales Enablement Solution Consultant role. I was focused on supporting our field reps and building out a sales enablement program. That’s the foundation of how I got here.

I think it’s tremendously important for anyone who’s in enablement to have known the experience of carrying a quota on your back – knowing that it’s feast or famine. You can have the best quarter of your life and go on vacation and the next quarter you’re eating ramen for dinner. That experience really allows me to connect with my audience. 

On the importance of sales leadership enablement…

I realized pretty quickly that enablement was something I would really enjoy because it combined two things I was passionate about: selling and teaching. 

There’s no better place to learn about sales enablement than Salesforce. One of the areas I was focused on was sales leadership enablement. My boss at the time realized that the key to having a successful enablement program is having sales leaders be really strong in their managerial skills and invested in the enablement programs. 

You will not be able to scale an enablement program unless you have sales leaders on your side enabling the enablement. That was a big piece of what I took away from my program there – how do you really empower leaders to empower their teams?

On iterating your sales enablement program…

The wonderful thing about being at a company as long as I have been at Optimizely, is that you get to see the company change throughout the years. I remember I used to get so bogged down in analysis paralysis. What is the perfect onboarding program and how do I build it correctly? The best thing you can do for an onboarding an enablement program is to just build it. I’ve come up with this tagline of ‘iterate to perfection’ and that’s exactly what we’d done.

When we were younger, we built a really engaging program where you came to headquarters for two weeks and we taught you everything you needed to know. That really did work for a while. However, we began hiring more field reps, moving up market and selling less of a product and more of a solution. It wasn’t cost effective or scalable so we realized it needed to be digital. 

We’ve evolved onboarding so many times to make it more efficient, more scalable for the field, and to help drive success. It’s all about evaluating where you are at, understanding where you need to be, and then making iterative changes along the way because you’re never going to get a home run on your first try. 

Over time, the needs of the field change and the needs of the business change. Being able to get it done, get it done well, but then building on that to make it better and better is the key to success.

On the importance of moving your onboarding online…

We moved about 70% of our onboarding online leveraging WorkRamp. Many of the sessions we used to do in person were just our leaders talking about the products – you don’t necessarily need to be in the classroom for that. 

We wanted to make a digital program where they could digest 100% of that knowledge online, then come to headquarters and participate in live activities. Now, we’re more focused on applying what you learned in a real life scenario. The program is significantly shorter and much more dynamic. We’re more focused on transforming behaviors and seeing learnings applied – as opposed to just instructing and teaching. 

On building strong relationships with sales leadership…

If I could go back in time, the one tip I would give myself is to truly connect with your sales leaders. Know their pains, know their challenges, and make sure they understand that you’re there to make their team more productive. They will make or break you. If you have a leadership team that doesn’t think you’re providing value, it doesn’t matter if you build the most beautiful, fantastic, well-designed program in the world. 

Realistically, enablement programs have between two and seven people supporting hundreds of reps. You can’t scale yourself. It’s the managers that drive everything. Being their ally and their resource will make all of the difference. I would say to myself  “Katie, go talk to that SVP of sales. Talk to that frontline manager. Talk to the person sitting across from me.” They have their customers – but they are my customers. How do I give them what they need and best equip them to be successful in their job?

Watch the rest of the interview here:

A big thanks to Katie and Optimizely for chatting with us and sharing their best practices.