WorkRamp Communities is now available.

Driving Remote Learner Engagement at Square, Hopin, TripActions, Shopify, and More

Over a year into remote work, we’re starting to settle into a routine, but with an odd emotion looming over our heads – we’re languishing. We’re not burnt out or depressed; we’re simply feeling stagnant in our lives.

Unfortunately, this feeling of blah seeps into how we perform at work. It impacts us in a way that’s so fundamental to working and succeeding in our jobs; we have a hard time finding the motivation to learn. 

In this edition of Top Female Voices in Learning, Enablement and Training, leaders discuss how their teams are supporting their remote learners through these challenges, initiatives to drive learner engagement, and make learning enjoyable again. 


Extend Grace to Yourself as a Learner

Shawnee Robinson, Square

Shawneé leverages her 10+ years of experience in public, non-profit, and corporate education, to provide leadership in the development, management, and implementation of learning solutions.

What does it take to be a successful remote learner?

Balance and time management

In a world where work and training are primarily remote, the learning experience for new hires and tenured team members can be overwhelming. New hires as well as established sales reps have to balance time around virtual instructor-led training (VILT), asynchronous online learning, and work events, on top of their daily responsibilities. Creating blocks in your calendar is a good practice to help with balancing these things. Setting aside time for training is just as important as pipeline management. Training allows sales representatives to have the competitive edge in terms of product knowledge, enhanced communication, sales skills, and efficient use of tools. Armed with these skills, sales reps will have what they need to close deals and increase revenue.

Clear and actionable communication

Do not be afraid to speak up if you have questions about content, next steps, or where to find resources.  Be sure to let the instructor know or ask your manager for assistance. Being in our homes, we do not have the luxury of asking our neighbor if we are unclear about a topic in the VILT or e-learning modules. My suggestion is to reach out via chat, slack, or email to your instructor, teammate, or manager. Within your preferred communication channel, include your specific question and provide as much detail as possible. Sending the problem, where you have already looked, and/or screenshots, will help give you the best solution to your problem. 

Extend grace to yourself

It is easy to become overwhelmed with the pressures of work and life – finding time to learn can certainly add to that. At times, thinking about how to get it all done can seem daunting. One practice that can alleviate the pressure is extending grace to yourself as a learner. Recognize when you are feeling overwhelmed and take breaks as needed. During these breaks take a walk, phone a friend, or whatever makes you happy. Be sure not to beat yourself up for not finishing your training by a certain time or for not understanding something new. Take a pause, but also hold yourself accountable for finishing by a new, reasonable deadline. 

What are some initiatives you’re working on to support your remote learners and drive engagement?

Our amazing Sales Enablement and Productivity team has worked hard and pivoted to support our decentralized workforce. The problems we are solving include scaling our new hire onboarding program, sales coaching remotely, and increasing product knowledge. We have found the solutions to these issues by: 1)Transforming our onboarding program to a blended-learning model that includes e-learning and VILT.  2) Utilizing technology to record sales calls and provide asynchronous feedback and coaching. 3) Launching interactive, on-demand e-learning and certifications on products, tools, and processes. Implementing these initiatives increases autonomy for when learning events take place as well as provide the necessary support with training and interventions.

Square is hiring for 600+ roles across the globe.


Meet with Purpose & Learn “In Flow”

Nikki Schanzer, Hopin

Nikki is currently the Head of Sales & GTM Enablement at Hopin, where she’s taking her knowledge and skills from years of direct selling in tech and leading the enablement function at Dropbox to build and scale a new function and team in order to best support the sales org.

What does it take to be a successful remote learner?

Remote learning is new for many of us and we have to over-communicate in a way many of us haven’t before (in a non-remote environment).

A few things to consider when remote learning:

Think through how your organization shares information: Are they using Slack, email, a content repository, a learning management system, or is meeting over Zoom/Google Meet a regular thing? For remote learners, it’s imperative to understand the cultural aspects of company communication so they can align quickly, connect in a streamlined way, and ensure they’re picking up the nuances of how to approach learning based on how the company provides it.

Meet with purpose: When you’re learning, it’s important to sync up with folks who are viewed as experts so they can give you information that gets you to the answer faster. Coffee chats are great and definitely serve a purpose, but being intentional is incredibly important as you’re looking to learn. Pro tip: Ensure you have an agenda and a few questions written out prior so you make the best use of everyone’s time!

Schedule “learning” time [“In Flow” Blocks]: We’re all constantly distracted by notifications, so it’s imperative to clear distractions and show up to learning knowing that you need head’s down time to do so. Whether it’s live training, video content, or reading, it’s important to schedule this time in and put away your devices and shut off notifications. Note: A 30 minute block is more than likely not going to cut it.

Find your approach: What works best for you? What makes you feel truly engaged? I find that I’m a note taker and I’m very visual, but really, that only goes so far. I need hands-on experience to truly feel comfortable. Think through what allows you to retain information and try to approach learning aligned to that.

Speak up: For many, this is uncomfortable and something that may take practice. Even the consideration of speaking up forces you to pay attention more closely, so whether you ask a question, make a comment, add something to the chat, etc. – it’s a great forcing function to stay present as you’re learning. Pro tip: If you have a question, you can bet others have the same one. It can help give you courage to ask when you know you’re helping others.

What are some initiatives you’re working on to support your remote learners and drive engagement?

Technology is more important than ever in a remote learning environment. In fast growing companies, you’re building constantly, and you need to get “just-in-time” information to sellers so they can continue to be at their best. I’m seeing newer companies come into the market to solve problems like this, which I’m genuinely excited to see. For enablement folks, we have to figure out how to strike the balance between giving reps the information they need to know to ensure they’re set up for success without taking them away from their day jobs for too long.

A few initiatives I’m working on currently include: a hybrid approach to new hire onboarding in a remote environment (live vs. video vs. LMS content, etc.), a regularly scheduled bi-weekly call that reps come to in order to get the information that’s top of mind (followed by a newsletter so they know where to go to find the information), and implementing technology to support remote learning for new and existing reps. I’m building from the ground up, so it’s an exciting time to think through what’s possible with a clean slate! 

Hopin is currently hiring for a Sales Enablement Specialist, Sales Operations Specialist, and Head of Deal Strategy.


Be Relentless with Your Discipline

Hannah Clinton, TripActions 

Hannah Clinton is a Director on the Global Sales Enablement team at TripActions, a modern end-to-end travel and expense management platform that enables businesses to build, manage and scale a world-class corporate T&E management program with ease. 

What does it take to be a successful remote learner? 

Being relentless with your discipline! Ultimately it requires a large amount of self motivation and a sense of responsibility to do this well. I like to approach remote learning in a similar way to physical training – create a daily habit, calendar block time when you know you are at your most switched on and ensure the environment you do it in is comfortable and without distractions. 

One aspect of remote learning I feel can get overlooked is the importance of a sense of community, by which I mean a group of people who are going through the same learning journey, at the same time, having a platform to connect with each other and share thoughts. For me this adds a sense of camaraderie that I enjoy and it’s been a highlight of remote learning during the last 12 months. 

What are some initiatives you’re working on to support your remote learners and drive engagement?

Over-communication has been key to supporting our remote learners so we have become maniacal about this. For each program we set up a community group prior where we detail the pre-read requirements, introduce them to their presenters, facilitators and team mates and start to build excitement for the specific course. 

Our sales enablement programs are centered around a Bootcamp Series which we have naturally had to translate into the virtual environment. In the instructor led sessions themselves our strategy is to encourage active participation. We do this using live polls, the chat function in Zoom, Kahoot! quizzes and virtual breakout sessions with dedicated coaches. I try to share in the group’s vulnerability as a presenter and make people feel comfortable to engage in the way they feel happiest. We added some gamification into the virtual sessions by way of a participation leaderboard and building on this we are in the process of introducing badges as we’ve seen this work well in other parts of our business.   

An initiative we introduced to drive overall program engagement is visible C-level sponsorship. As an example, our CRO now actually kicks off our sales methodology remote bootcamp. This helps create that burning platform for the training from the top down. We have found that once participants hear that a program is worthwhile investing their time in directly from our executive team they tend to give it that extra level of dedication.

TripActions is hiring for 3 Sales Enablement Managers in Austin, New York City, and SF Bay Area.


Lean into Visual & Collaborative Learning

Seema Jain, MURAL

Seema Jain is the Head of Sales Effectiveness at MURAL. She has over 15 years of consulting expertise in advancing sales effectiveness for enterprise brands, leveraging her passion for design in the shift to virtual customer engagement and virtual seller enablement.

What does it take to be a successful remote learner and what are some initiatives you’re working on to support your remote learners and drive engagement?

You have likely seen the meme that credits COVID-19 as the greatest factor accelerating a company’s digital transformation strategy. The pandemic propelled us into new ways of selling and learning — in terms of how we engage with prospects and customers and how we enable our reps to facilitate those conversations, now suited for the virtual reality we find ourselves in. 

At MURAL, we’ve seen organizations pivot overnight to virtual-first best practices to improve customer engagement including pre sales call planning, discovery facilitation, account planning, and stakeholder mapping. Simply keeping prospects and customers engaged on video calls alone is not enough. Our sales team is employing MURAL to engage customers in a two-way conversation for better collaboration, participation, and co-creation that ultimately leads to improved win rates and increased ACV.  

On the flip side, the Sales Effectiveness team has redefined virtual enablement to train sellers in new skills, deliver new hire onboarding, host quarterly kick-offs, and assess performance — all optimized for a remote setting, which has reduced ramp time and improved quota attainment. We recently kicked off our fiscal year with a Go-to-Market event adapted for the virtual work environment, which included a digital swag bag, interactive itinerary, abbreviated agenda, virtual avatars, and interactive icebreakers. Our programs have leaned into the art of remote facilitation, scaling visual collaborative selling through MURAL frameworks and sales methodologies.

While I can’t wait for life to return to normal, visual collaborative selling is here to stay. Sales and customer engagement have come so far in such a short time, we will never go back. The brands with the foresight to prepare their teams for a virtual-first approach will win. It’s been incredible for me, being on the forefront of this sales innovation at MURAL and enabling our customers to do the same.

Seema is currently hiring for open roles on her sales enablement and solution consulting teams!


Be Organized, Purposeful, and Disciplined about Learning

Timea Bara, Nextdoor

I’m the Head of Sales Enablement at Nextdoor, where I’m building and leading global sales learning and development for the growing revenue team, working with many cross functional groups from product to insights to empower our field to become valued partners to our customers and help them realize value.

What does it take to be a successful remote learner–and what are some initiatives you’re working on to support your remote learners and drive engagement?

Remote life is hard, the mental and sensory overload is very real, and learning in this environment can be challenging. It’s been a year since most of us have seen our colleagues, had a good in person white boarding session, had an opportunity to ad-hoc pick someone’s brain etc. What I’m hearing most often from sales people is that the organic learning – hearing their coworkers on the phone, picking up on tidbits from other conversations – is what they miss the most.

In my opinion, in order to be successful NOW, one needs to be very organized and purposeful, I should say disciplined about learning. For me it boils down to:

  • deciding on one or two focus areas for a quarter
  • having self awareness to understand what learning works best for you (i.e. buying both the audio and the physical book to switch in between, practicing things, etc.)
  • creating “unmovable” learning blocks in your calendar
  • having accountability measures in place

There are a lot of ways we can support remote learners. “Democratizing” learning – by allowing people to learn on demand, and offering them different modalities (resources, videos, podcast format etc) is one important element. I also introduced a structure of majors and minors for product training, where things that require a behavior change will be handled in a “live” session versus pure knowledge plays that can be videos consumed over a specific timeframe. Leadership buy in, leading by example and making learning a priority is also very important.

Nextdoor is hiring for a Sales & Onboarding Specialist and a dozen of roles around the globe.


Weave Small Bursts of Live Trainings with Asynchronous Work

Daniella Bellaire, Shopify

As a revenue and strategy executive Daniella’s primary focus has been on building and scaling revenue organizations in both startup and high growth companies. In her current role as Global Head of Enablement at Shopify, she is dedicated to building a best-in-class revenue enablement organization to drive the growth of both internal teams, revenue, and customers. Daniella cares deeply about people development, solving problems to unlock growth, and mentoring the next generation of revenue leaders.

What does it take to be a successful remote learner?

There is a bit of a personal element to this that is unique to the learner. Understand how you learn and in what type of environment. As an ongoing learner myself, I like to keep it simple and stay organized. I break out my learning objectives by day or week, carve out that time in my calendar to ensure that I have no distractions in the space of my choice. Remote learning does not mean independent learning. If you are someone who learns by talking through problems and ideas then pairing up with peers is a great way to learn together and challenge each-other. This also helps with engagement and relationship building as a bonus.

What are some initiatives you’re working on to support your remote learners and drive engagement?

We really went back to foundations at the beginning of this year. We committed to rebuilding and iterating on most, if not all, of our current enablement and onboarding practice for revenue. As a company who has made a commitment to be digital by design indefinitely, meeting our learners where they need they way they need is so important for us to fuel their success. Our programming now consists of small bursts of virtual real life facilitator led training as well as async work. We have invested in new technology to help us drive engagement on a peer to peer level as well as in broader group settings. We are now able to track participation, progress on content, measure content retention with small assignments, and align regional leadership coaching for reinforcement. This will be an ongoing iterative investment we make all year.

Shopify is hiring for Sr Sales Enablement Lead (AMER), Operations and Enablement Manager (AMER), Enablement Lead – Technology Services (CAN), and Partner Enablement Manager (APAC).


Get Competitive to Stay Engaged

Daphne Valentino, INFUSEmedia

Daphne Valentino is Marketing Ops and Sales Enablement Manager at INFUSEmedia, where she oversees sales development humans, sales enablement robots and other marketing things.

What does it take to be a successful remote learner–and what are some initiatives you’re working on to support your remote learners and drive engagement?

Remote learning (and working for that matter) requires a lot of self-discipline to balance success in both your personal and professional life. When I first stepped away from the traditional office environment, I found it was very hard to ever “disconnect” from work. When you are no longer in a traditional and structured environment, it becomes even more important to be committed to your own wellness in order to be successful.

At INFUSEmedia, we have taken a unique approach to drive engagement and support our remote workers by holding competitions for both individuals and teams. Zoom meetings have also provided an amazing way for us to still have our coffees and lunches together while chatting and in meetings. Though remote work makes it challenging to maintain a sense of connection at times, we make it a priority to foster camaraderie and make it a part of our culture —  whether it’s via Zoom, appreciation pings, or posts (just to name a few). This approach has offered us a unique opportunity to peek through the doors of our coworkers’ lives and get to know each other even more, and we’re leaning into that as best as we can.

INFUSEmedia is hiring for dozens of roles.


#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!

Complete the form for a custom demo.


Ready to Get Started?

Get in touch to learn how WorkRamp can help you achieve your training goals.

Request a Demo