Sr. Manager, Solutions and Systems Enablement, DocuSign
How do you define enablement?
Our mission statement says that we equip our sales and customer success reps with the Knowledge, Skills, and Tools that they need to succeed and do the work of their lives. I love that because it leaves a wide open playing field for us to help reps be successful. More than just training (though that is important and not a dirty word), it’s about doing anything that we can to help our teams achieve their goals. Enablement is all about breaking down barriers and pulling together resources to accomplish big aggressive goals.
Describe your current role.
I’m currently managing a team of 8 enablement professionals. We lead global initiatives related to three primary areas of oversight - Product Enablement, Systems & Tools Enablement, and Process/Methodology. This includes managing and governance of our core enablement platforms (LMS, content management, and coaching/conversation intelligence software).
My team partners with our regional counterparts in NA, EMEA, APAC, and LATAM to drive these global initiatives with regional delivery and personalization.
Briefly walk through your journey to get where you are today.
I’ve always been passionate about people and helping them achieve their goals. For a while, I actually thought about taking that passion into counseling and working with nonprofits, but at the same time I had to pay the bills so I ended up in sales. What I loved most about sales was the ability to help my customers achieve their goals using our technology. My most satisfying achievements were when a customer would be featured in a case study or speak at a conference talking about how satisfied they were with the solution. Meanwhile, I was always the one taking on side projects to help my team (mentoring new hires, organizing extra training sessions, team building events, etc). So when I had the opportunity to pursue enablement as a career path, it was a natural fit for me to move into a role where I could help my colleagues achieve their goals.
I started out in enablement leading onboarding programs for new reps in a variety of roles including sales and customer success. As DocuSign pivoted from a single-product to a multi-product solution company, I had the chance to move into building product enablement to help our teams understand the entire Agreement Cloud portfolio. After that, I built out our systems enablement function to drive adoption and effectiveness in how we leverage the software tech stack that we arm our reps with.
About a year ago, I had the opportunity to move into this leadership role which allows me to pursue my passion for helping people achieve their goals very actively for the amazing members of my team. I’m so excited to be able to invest in this team of smart, capable people and do whatever it takes to empower them to succeed both on their business projects as well as their personal goals.
What’s your proudest accomplishment?
I’ve been really lucky to be able to participate in some of the coolest and most impactful projects in my time at DocuSign. But by far my proudest accomplishment now is building my current team. When I took on this leadership role, there were two of us on the team after some transfers and promotions. So I had to quickly start recruiting while also delivering on our previously committed projects. To a person, every one of the new members of the team have excelled my expectations and are receiving accolades from business partners across the company. The team has now grown to 8 people (and actively hiring!). And while this is incredible to see the results and the output in a fairly short time, the best moment for me was during a team summit that we held towards the end of last year. We spent a week together over Zoom collaborating and planning for our big goals and priorities for the year. By the end of the week, not only were we not all sick of each other after 6+ hours a day on Zoom with the same people, but we’d actually grown so much closer together. So the camaraderie and trust that we’ve been able to build with a brand new team of very diverse people and backgrounds is the thing I’m most proud of.
What’s your advice to someone getting started in enablement?
Two pieces of advice. First of all, never lose sight of your primary audience - the field reps. An effective enablement function acts as the bridge between the field and the back office, advocating for sales and success reps so that we deliver just what they need and building programs for them that are engaging, impactful, and effective. My second piece of advice is to embrace the unknown with an open mind. Enablement is a new enough function in the business world that for many companies there isn’t a playbook or some set of rigid guidelines to follow. So while this can feel ambiguous and scary, I think that it actually empowers creativity and new ideas. The enablement community is full of people who are eager and willing to share their experiences and brainstorm with you for how to creatively accomplish your goals, so use these networks and resources to bring in fresh perspectives to the rest of your company.
What are you doing to develop yourself?
I believe that one of the core traits of a successful enablement professional is having a growth mindset, constantly gaining new skills and experiences, and at DocuSign we are lucky to have a generous education reimbursement program. So I take at least 2-3 courses a year on subjects such as strategic leadership, change management, program management, etc. I am also currently pursuing my CPTD certification from the Association for Talent Development. Finally, I have a leadership mentor who I meet with regularly to continue to grow and develop as a leader.
Connect with Jesse on LinkedIn!