Community Spotlight: Kyle Pickett


Kyle Pickett

Sales Enablement Manager at Remesh


How do you define enablement?

For me, enablement is making your team as successful as possible. I break that down into a few things: effectiveness, strategy, and learning & development. Strategy and effectiveness show up in a company’s sales processes, collateral, and anything the sellers need to be equipped for the front line. L&D is the most important part of enablement, in my opinion. You can break this into product training, onboarding, and leadership development. These are all the methods by which we can stimulate the success of our sales reps.


Describe your current role.

I oversee the entire revenue enablement function at Remesh - a one-person show! I strive to make 4 teams successful: SDR, Enterprise AE, Customer Success, and Project Management. I constantly am consulting with key stakeholders across the organization to develop the revenue enablement plan. At Remesh, we focus most heavily on product training. We release features on an every-2-week basis, so I have to make sure the sellers are delivering demos with knowledge as fast as the product team is delivering features.


Briefly share your journey that got you to where you are today.

I started as a musical theatre major in college and I really loved performing, but the career trajectory made me nervous because I love stability. Before that, throughout high school and college, I volunteered to mentor younger students in theatre and overall performance. It was in those moments that I really developed my love for learning and development. Along the way, I found the perfect marriage - sales and education. I found my second love working at AT&T and working my way through the retail industry throughout college. From there, I transitioned into a program manager role for sales execution. I had the pleasure of training SDRs and mid-market AE’s throughout Los Angeles, Las Vegas, and Nashville.


After AT&T, I found myself at WeWork, specifically for the Flatiron School. Flatiron School’s mission really resonated with me - to change lives through education. I like to say I was a Sales Manager by day and Sales Enablement Manager by night. If you know start-up lifestyle, you’ll know exactly what I’m talking about. While at WeWork, I volunteered at Out in Tech as a youth mentor to coach younger LGBTQ+ students and help them find jobs within the tech sector. After WeWork, I settled into my current home - Remesh. I never would have thought in all my years on stage that I would end up on a sales stage, performing for sellers full-time.


What’s your proudest accomplishment?

My proudest accomplishment is the pivot that we made at Remesh for our sellers when Covid hit back in March. When the pandemic started, we found ourselves at several dead ends in developing ongoing training. Everything we once knew, we had to throw out the window. I set out to develop a blended learning and coaching program for our revenue teams.


The first thing we had to do was consult with key stakeholders in revenue leadership, marketing, and product. I really wanted to dive deep into figuring out what the sellers needed to be successful in remote work. Our second consultation was the audience themselves - the revenue team. I wanted to understand how they wanted to learn since lecture-based learning was completely out the door.


I work on projects as if I’m building a product, and that’s the philosophy I took with designing a Covid pivot roadmap. I scoped the work through discovery, design a roadmap, work in 2-week sprints, and develop a product management board for transparency for my stakeholders. I built a blended learning and coaching program for our revenue team using new systems. I added Lessonly into our stack, while strengthening our existing systems: Zoom, Outreach, and Knowledge Resource Center. I wanted to give sellers autonomy with training, while still ensuring they were adopting the knowledge. Our new LMS proved to be the biggest asset during our Covid pivot.


In a qualitative research conversation we held through our platform at Remesh, we learned that 76% of sellers felt more comfortable in consuming knowledge while working remotely and 82% agreed it was more powerful than lecture-based learning.


What’s your advice to someone getting started in enablement?

My number one piece of advice for someone getting started is to find a mentor! Enablement is such a niche field, so it’s important to find someone who is already in the field who you can learn from. My second piece of advice is ABL (Always Be Learning). You can find numerous resources through books, Slack groups, and other people in the field. My last piece of advice is something that someone told me - find the enablement role that fits you best and stick with it. Enablement can mean many different things to different companies - there will be a role for you!


What are you doing to develop yourself?

I personally set a lot of stretch goals for myself in development. Most recently, I’ve started taking voice lessons once a week to get back in touch with musical theatre. I find a lot of comfort in working out, so I’m constantly working with my personal trainer to develop my fitness goals. I find that sometimes we can get caught up in our day to day and lose track of taking care of ourselves, so I want to buck that pattern. I personally flipped the Kirkpatrick Training Evaluation model back on my personal life. I’ll show some examples below:

  • Reaction - Am I happy with what I’m doing currently? How satisfied am I in my day to day? What could I be doing better?

  • Learning - Skills to teach myself in an effort to combat the questions above: voice lessons, fitness programs, yoga, meditation, etc

  • Behavior - Am I able to use these skills to make me more satisfied in my day to day? Did voice lessons change the way I speak and release tension in my jaw? Did the fitness program give me more energy throughout the day?

  • Results - It’s really hard to track qualitative personal performance, but for me it showed up in everything from the time I went to bed to the new songs I’m learning to sing.

Connect with Kyle on LinkedIn!

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