Director, Enablement at KeepTruckin
How do you define enablement?
Enablement is the science and art of empowering customer-facing teams with the information, skills, tools, and discipline they need to thrive in their roles.
Describe your current role.
I lead a global team of 18 enablement professionals, supporting a sales and customer success team of 700+. Key challenges we face are a team that is distributed across multiple countries and offices, a company that scaled quickly and is now focused on refining infrastructure, and (as always!) bandwidth constraints. We focus our efforts in 3 different areas: soft skill development, GTM Initiatives (product and process training), and Infrastructure (onboarding programs, methodology, certification).
Briefly walk through your journey to get where you are today.
I'd always wanted to be in either education or law. I studied philosophy with plans to proceed to law school. Life had different plans, and due to some health issues, I was forced to pause my studies early on. As I recovered, I found myself with a large amount of medical debt and serious questions about whether or not a career in law was the best choice.
I took a full-time job at Nordstrom, began clearing my debt and got my first glimpse at careers in sales. While very different from the B2B environment I support today, I remember loving the energy and hustle of sellers. I worked my way into corporate learning and development at Nordstrom and grew from training frontline team members to managing trainers, to managing training supervisors.
Wanting to find my way into a startup, I took a chance and lower title to join Lyft, with a focus on training compliance. Then, I found my way to a smaller startup, KeepTruckin, where I am today. As I look back on all of these experiences, what stands out to me is the diversity of subject matter I have been responsible for training. I have trained or led teams that have trained Customer Service, Leadership, Collections, Disputes, Compliance, Sales, and Customer Success. It's a great reminder that regardless of background, with the right hustle and creativity, anyone can create success in sales enablement.
What’s your proudest accomplishment?
This year, one of our key challenges at KeepTruckin was the lack of uniformity in the sales process, particularly on larger sales teams. This not only led to difficulty in managing and forecasting for those teams, but also difficulty in diagnosing problems impacting the teams' performance.
To help us diagnose, we began an intensive certification exercise for one of our global teams (400+ in this group). We identified the subject matter they needed to know (including process, product, sales motion) and conducted testing (mock calls, mock demos, multiple-choice tests, CRM Sandbox simulations). Certification allowed us to acquire tremendous data around what needed the most work. Moving forward, it will also enable us to show the gaps we have closed when the team is re-tested. Having this hard data to show stakeholders also led to tremendous buy-in. Stakeholders readily partnered with us to correct & document broken processes and began getting behind all of our training efforts (even making training completion part of the team's KPIs). While we're still wrapping up final tests, there have already been tremendous, data-driven insights that we can share with execs and that will guide prioritization of our work for quarters to come.
What’s your advice to someone getting started in enablement?
Master the basics of operational excellence and project management and know how to map out competencies. In Enablement you can often be considered the trusted advisor, particularly when we can add a basic structure or framework to performance conversations. Not only does the whole team get the work done faster when we add structure, but we often gain buy-in and influence we may need later.
What are you doing to develop yourself?
Reaching out to mentors and colleagues in my network. Given that my entire career has not consisted solely of enabling sellers, I know I have plenty to learn and enjoy learning from fellow enablement professionals. Of course, reading is critical as well. I am currently re-reading The Challenger Sale to see what we can use from this and other methodologies within our sales organization.
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