Kyle serves as the Director of Sales Enablement at Guidewire Software. Guidewire combines digital, core, analytics, and AI to deliver a property & casualty insurance platform as a cloud service. 400+ insurers, from new ventures to the largest and most complex in the world, run on Guidewire. In his role, Kyle and his team support a team of 220+ sales managers, account executives, and solution engineers in 13 countries. Kyle is passionate about creating a world-class enablement experience for sellers by challenging the status quo, pioneering innovative techniques, and incorporating new technology. Before joining Guidewire, Kyle held roles in enterprise software Sales, Product Management, and Professional Services at a Fortune 100 company. He moonlights as a studio bass guitarist and a children's book author.

Interviewed by Nimish Vohra

// What significant challenges are you facing as a result of COVID, and how do you work around them?

Guidewire Software is a global enterprise software company. We have had a distributed team of some sort for most of our two-decade history. However, having everyone working from home was certainly an adjustment! We quickly learned that attempting to virtually replicate the kinds of internal meetings we were having in person wasn't optimal. Meeting frequency, duration, facilitation, and tools all had to be adjusted. It was an excellent opportunity to re-evaluate which meetings needed to happen at all. The temptation to multitask is so much stronger when you're not in the same room. We've had to focus on creating shorter, focused, and more engaging meetings.

Regarding our customers, there was a period of inaction at the beginning of the pandemic, like in most industries. We've had to be more creative and flexible in handling remote sales demos and workshops to keep the sales cycle moving while still meeting the sales event's objectives. For example, providing short, pre-recorded demos to customers ahead of a live remote demo allows the live demo to be much more focused and engaging. Our Sales Enablement team is adapting our sales playbook to include how best to execute the plays remotely to help on this front.

// Have there been any unforeseen consequences? How did you tackle those?

Who could have expected "Zoom fatigue" to enter our vocabulary? At Guidewire, we certainly experienced an increase in both the number and duration of meetings, especially early in the pandemic. To combat Zoom fatigue, we researched and implemented best practices in our Sales Enablement events. In particular, we have shortened our sessions and focused them on fewer key takeaways. For day-long or multi-day events, we've shortened each day's duration and spread the sessions out over more days or even weeks. Instead of fighting against multitasking, we've accepted it as an unfortunate reality. We are inserting additional engagement points in the middle of our sessions to invite the audience back into the training every 15-20 minutes. Chat questions, polls, and exercises to put concepts into practice work well.

// How has COVID impacted seller productivity, and how have you been addressing this?

We've experienced two unexpected positives during this time. First, we've seen an increase in the adoption of sales enablement training, particularly on our recurring live training webinars. Sellers are no longer spending disconnected time on planes and in hotels. Some have eliminated an average of a day per week in travel time. We see this as an opportunity to help them fill that time with sales enablement sessions.

Second, we now have an excellent opportunity to provide sales coaching on more sales calls. Before the pandemic, more than half of our conversations with customers were in-person. It would be more than a little awkward for a seller to pull out an iPhone and ask to record the conversation for their manager. Currently, the majority of sales calls and events are happening via Zoom rather than in-person. It's much easier to ask permission to record the Zoom call and review the recording with a sales manager.

// Have COVID circumstances exposed any scope for optimization in your technology or processes?

Absolutely! Like most organizations, we are continually looking for ways to optimize. COVID has shined a bright light on some areas. For example, before COVID, most of our sales meetings occurred in-person, so we hadn't seen a need for a sales coaching platform to record those meetings for feedback. With so many more meetings occurring remotely, it now makes a lot more sense to invest in such a platform. These platforms can provide real-time feedback to the seller on tone and pacing, and make it easy for sales managers to watch a recording and provide feedback.

Additionally, we expect fewer in-person training events in the future. We are looking at ways to improve the asynchronous and remote sales enablement sessions we provide with new tools, reconsidered training frequency, and more. COVID has given us a new lens through which to look at all of our technology and processes. It would be unwise not to examine everything we do as a Sales Enablement team and look for areas to improve.

// Aside from a switch to remote training, has there been a strategic shift in your approach to sales training?

We have always had a globally distributed sales team at Guidewire. So, in many ways, the pandemic impacted our sellers less. However, when we look ahead to post-pandemic, we expect to have fewer in-person sales enablement events. We've been thinking about the best way to integrate self-service, live virtual, and a limited number of in-person training sessions for our sales onboarding and "everboarding" programs. We are also considering the number of in-person events in terms of a finite budget, which we will need to spend wisely throughout the year.

We've been seeing a shift in the training topics that sellers consume most. For example, there's now more interest in presentation skills, and we have responded by investing in remote presentation training. We are also amending our sales playbook to include additional collaterals, instructions to execute the plays remotely, and templates for collaborative tools like Miro.

// How have selling strategies been altered at your organization? Will this shape future strategy in a post-COVID world?

I don't think our sales strategy or process has changed much. We know the steps that help our customers make informed decisions. But how we execute those steps will need to change. Customers will drive most of that change based on their comfort level with in-person meetings. Guidewire serves property and casualty insurers, who are risk-averse by their very nature. We expect very few in-person meetings in the next 6-18 months, so we are investing in helping our sellers be as proficient and effective in a virtual selling environment as they can be.

Once COVID is safely in the rearview mirror, we expect to see a higher percentage of remote customer meetings, but not the 80%+ that some industry analysts suggest. If 20% of our meetings were virtual pre-pandemic, I would expect that percentage to eventually become around 40%. Having a clear strategy for which parts of the sales cycle are more effective in-person and which parts can be remote will be critical in the future.

// What are the lasting industry-wide changes that you expect to see staying beyond the COVID phase?

COVID has certainly accelerated changes that were already occurring. In all industries, buyers have become much more informed over the past decade. More and more, buyers are making decisions based on their own research and crowdsourced feedback, rather than solely relying on information provided by salespeople. The most effective salespeople add value to customers at every interaction. Sales Enablement teams can help by arming salespeople with industry trends, competitive intelligence, and customer stories in addition to company and product information.

Interestingly, we're seeing more people involved in buying decisions for our customers during COVID. The barrier to joining the conversation is lower with Zoom, so we're gaining access to more decision-makers in our sales events. On our side, it's also easier to bring more subject matter experts on calls to help answer questions from those additional buyers. The risk with this shift is that it is harder to keep the broader sales and buying teams in sync. Sales Enablement can help by investing in sales tools that make internal collaboration simpler and make communication easier.

// Are you looking forward to a return to business as usual? Please expand on this.

This period is the longest I've been at home in more than a decade, so I am certainly looking forward to some kind of return to normalcy! But I do expect the frequency at which we need to be in the same room will be less. There will be more focus on the "moments that matter." Those are things like introductions, delivering the business case, and final negotiations in the sales cycle. Those moments in the sales enablement journey include welcoming new sellers, conducting onboarding workshops, and hosting annual sales kickoff events. This shift will require us to get better at enabling our sellers asynchronously and remotely. When we do get in the same room, we will strip out anything that can be done remotely and only focus on those activities which should occur in person.

// What is the most significant learning you've taken from this experience?

COVID has reinforced my belief that every challenge is an opportunity to get better. The only thing you can control is how you respond to difficult situations and whether you come out in a better or worse position. Your organization may need to change its sales approach, redefine success criteria, or develop new skills. But you will go through COVID regardless, so you might as well get something positive out of it.