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Introducing #WomenLEAD—Female Leaders in Learning, Enablement, and Development That You Should Know

As we embark on a new year in Revenue Enablement, Customer Education, and L&D, we’re reflecting on the abundance of unexpected moments, challenges, and changes brought by 2020. In our #WomenLEAD series, we’ll be catching up with female leaders in the industry as they share how the lessons they learned in 2020 are guiding their goals and vision for the future. 

Be Confident in Strategy and Flexible With Execution

Ashley Crisostomo, Reddit

Ashley Crisostomo, Reddit

Ashley Crisostomo is a Principal Program Manager on the Sales Enablement team at Reddit, overseeing sales onboarding and go-to-market efforts.

What’s the most impactful business lesson from 2020?

For me, 2020 was all about confidence in our strategy, but flexibility and creativity in execution. The pandemic upended many plans that were set at the beginning of the year, but the business needs remain regardless of how much the workplace has changed. In 2020, we allowed ourselves to be creative in the ways we showed up for our internal teams–from new and interactive training modalities to reprioritizing the connections we make internally–all while using our original strategy as our north star. It was a hard year for everyone, so it was important for me to be a positive cultural force for our learners and XFN teams.

What learning initiatives will you focus (or refocus) on in 2021?

As we turn the corner to 2021, we are grateful that our business is growing more than ever – so we’re full speed ahead building upon the foundation set this year. We’re excited to onboard our biggest batch of new hires yet and double down on the “humble swagger” we’ve been developing with our sales teams as they go to market with new solutions for our customers.

Reddit is hiring for a number of open roles – including Sales Onboarding Manager and Learning Experience Designer on Ashley’s team!


Fail Fast and Pivot Often

Gabriella Petrone, Box

Gabriella Petrone, Box

Gabriella Petrone is a GTM Enablement Manager leading onboarding and sales enablement programs at Box, the Cloud Content Management company that revolutionizes how companies work by securely connecting their people, information and applications. 

What’s the most impactful business lesson from 2020? 

My biggest takeaway from 2020 was that change is the only constant. Moving to a virtual enablement landscape forced us to focus on all wins, big and small. This allowed us to fail fast and pivot with agility to achieve our goals. 

What learning initiatives will you focus (or refocus) on in 2021? 

In 2021 my main focus will be strengthening alignment with stakeholders and leadership, enabling a world class group of talent by up-leveling our GTM teams, and solving for a hybrid onboarding model when offices begin to open up.

Box is currently hiring for 80+ open roles in its Austin, Boston, Chicago, and New York offices.


Get Creative With How You Communicate

Lisa Thompson, Branch Metrics

As Enablement Program Manager at Branch, Lisa Thompson is dedicated to building a best-in-class enablement organization to serve internal teams and customers.

What’s the most impactful business lesson from 2020?

Moving remote made getting and staying aligned difficult. We knew that in order to be successful, we needed alignment with all of our stakeholders. For our international team members, we’d schedule meetings during their business hours, even if it meant a late night or early morning call for us. To sustain interest and engagement on different projects and initiatives, we’d share exciting updates with teammates via Slack. It forced us to be creative and strategic with how we communicate. 

What learning initiatives will you focus (or refocus) on in 2021?

This will be a big year of focusing on the user journey to provide the knowledge and resources that users need when they need it. This initiative is critical to drive self-serve enablement and scale our business. 

Branch Metrics is hiring for open roles on its sales and customer success teams. 


Practice Empathy and Self-Compassion

Megan Hunting, Intercom

Megan Hunting is a Senior Sales Enablement Specialist at Intercom, where she owns the global Sales Onboarding program and leads training for the global sales team. 

What’s the most impactful business lesson from 2020? 

Things happen that we will never be able to predict or control. That sounds negative, but there is a lot of power and peace to be found in accepting that and not resisting it. Focus your energy on the things that you do have control over: the relationships you have with your teammates and customers, the quality of your work, and the narratives you tell yourself. Life has a weird way of falling into place when we simply show up and do the best we can with confidence that things will work out. 

What learning initiatives will you focus (or refocus) on in 2021?

As a sales training team, we’re continually focused on ensuring our sales reps are uncovering real business pain in their conversations with prospects and customers, so that we can actually solve their problems and help their businesses be more successful. This means ensuring our reps are doing really thorough discovery, being empathetic partners, and understanding our customers and their businesses as deeply as possible. I’m looking forward to continuing these trainings in 2021 – hopefully together in the same room!

Intercom is currently hiring for open roles in its San Francisco, London, Chicago, Dublin, and Sydney offices.


Make Tough Decisions as Necessary

Brittney Frenette, Four Winds Interactive

Brittney Frenette, Four Winds Interactive

A Customer Experience Enablement professional at Four Winds Interactive, Brittney Frenette empowers and educates customers and customer-facing teams through strategic learning programs. 

What’s the most impactful business lesson from 2020? 

You can’t please everyone. I started with my new employer on March 1, 2020.  A mere two weeks later we transitioned to working remotely, as the business world adjusted to the pandemic. Being a new employee, not yet having had the chance to build interpersonal working relationships, I tried to make decisions that everyone would agree with. Those efforts resulted in my most impactful business lesson for 2020—the realization that making tough decisions is a necessary criterion for successful customer engagement and satisfaction, as well as impactful career growth and development. 

What learning initiatives will you focus (or refocus) on in 2021? 

As I navigate the next year of my career, my learning initiatives will include continuing to work on strong decision-making skills, team collaboration, and excellent customer service skills.  I will continue to strive for win-win initiatives, keeping in mind that success is a process of development, commitment, and perseverance. 

Four Winds Interactive is hiring for a number of positions in its Denver office.


Focus on Your Outcomes, Not the Details

Tori McGillen, Databricks

Tori McGillen manages the sales new hire program, creates training content, and facilitates onboarding classes for client-facing teams at Databricks as a Sales Performance Program Manager.

What’s the most impactful business lesson from 2020?

Don’t get too attached to how you implement ideas today—focus on your desired outcomes instead. When our sales enablement team pivoted from in-person to virtual training in March of 2020, reframing our training and activities around a virtual classroom meant we had to be very deliberate about what we wanted to accomplish. Approaching these challenges from the ground up was more effective than trying to fit in-person training styles into a virtual world—it was painful, but worth it, to completely change up some of our “in-person” ideas that had worked well before.

What learning initiatives will you focus (or refocus) on in 2021?

I’m interested in upgrading our sales training content strategy to help better connect our subject matter experts with our sales teams. We’ve put a lot of work into our instructor-led training this year, and now it’s time to give the same level of attention to the content that teams access after onboarding. As we continue to grow, we’ve got to make sure the training content keeps up—aligning with business initiatives and messaging, easy to find and access, and measurably driving results.

Databricks is currently hiring for 150+ roles in San Francisco, New York, Amsterdam, Toronto, and London.


#WomenLEAD is a collection of stories, interviews, and advice from women who are spearheading the future of Learning, Enablement, and Development. If you know an inspiring leader in L&D, Revenue Enablement, or Customer Education who should be featured in a future installment, please get in touch!

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