Real Talk From The Trenches: How to Sell Enterprise Software Remotely

Nicole Wojno Smith on Apr 28, 2020

Panelists from Tackle, Seeq, Cockroach Labs, and GitLab open up their playbooks on how to sell enterprise software when working remotely and how to use Cloud Marketplaces to accelerate deals.

The impact of the Coronavirus pandemic has been felt, at least to some degree, in every industry. How can enterprise software sales teams, who may be adjusting to moving from in-person meetings to remote-first sales make the most of selling remotely?

On Tackle’s webinar, Real Talk from the Trenches: How to Sell Enterprise Software Remotely, we talked to four experts whose organizations have embraced remote-first selling for many years and are also using Cloud Marketplaces to sell faster. Don Addington, Megan Buntain, Jen Murphy, and Mayank Tahilramani all shared their perspectives on topics such as:

  • How have your teams shifted their GTM strategy and success metrics, and how you engage with customers to align with the current COVID environment?
  • How do you enable your sales team in a completely remote environment? What tools help you with this?
  • What attracted you to Cloud Marketplaces, and what success have you seen through it?
  • What are some of the challenges you have selling via Cloud Marketplaces?

Here’s what we found out.

It’s essential to focus on helping customers in times of change or uncertainty

There was a consensus on the importance of being there for customers, now more than ever. Between reviewing how your company can best serve customers right now and opening up additional communication channels, there’s a big shift towards empathy.

Jen Murphy, Head of Channel Sales at Cockroach Labs, shared that her team is focused on supporting customers across all channels and aspects of her business.

“We’ve extended our support via a Slack channel for customers using the open-source and our hours of operation for support. We’ve also come up with some unique ways for helping the global enterprises who are self-hosted to get engaged and move forward with some projects with less risk involved.”

Jen also noted that her company is “really looking at what each customer segment is going to need to be successful and helping them down that front. “

Megan Buntain, Director of Cloud Partnerships at Seeq Corporation, is also taking this time to assess what customers need. “We have looked at the use cases and the business value that we offer to customers, and asked, ‘How is that relevant today? What is the most relevant, and what’s driving business continuity for customers more efficiently?’ That way they perform and thrive as we come out of the COVID crisis.”

Mayank Tahilramani, Sr. Alliance Manager at GitLab, shared how they’ve enabled their sales team to shift the budget conversation from OpEx to CapEx.

“Advocating how GitLab can help the customer or the organization realize the investments they may have already made to the Cloud provider. That dovetails into the Marketplace discussion where you can actually tap into an OpEx budget instead of a CapEx budget. Particularly during these times where you start having a different conversation around budgeting and how you’re actually going to procure, and what the value proposition is, and what the return on investment is, particularly during a time where everyone is remote. So software can help augment the gap caused by the remote workers.”

Don Addington, CRO at Tackle, talks about how we’ve used weekly Office Hours to educate prospective buyers on Tackle and Marketplace.

“Now more than ever, the messaging of, to get a deal done is never an easy thing, in any environment. It’s been fun to educate some of our prospective buyers. Hey, if you’re looking for other routes to getting business transacted right now, we’ve seen the Marketplaces be an easier path because it’s an established relationship that you’re sourcing software through. I think we’ve been able to help provide some ideas.”

“We’ve also done some things like we started offering weekly Cloud Marketplace Office Hours. We normally travel around a lot and go to a lot of Cloud provider events and obviously none of us are doing that anymore. In a way, it’s cool because we’re all in the same boat. It’s not like one person trying to pull everybody else into a remote conversation. Everybody is doing some events like offering up Office Hours where we don’t have that exposure by traveling. A lot of people are coming to us and asking us whatever they like.”

Communication tools and documentation keep everyone on the same page

When it comes to communicating with remote sales teams throughout the day and keeping tasks on track, the right tools and documentation are key.

When asked how his team communicates better while working remotely, Mayank shared that, “we communicate internally, asynchronously with a single source, and we’re known for our GitLab handbook where we write almost every aspect of our company down.”

“You can find exactly what we’re doing, how we’re doing it. We’re a very transparent and open company from our roadmap to our business operations, to even getting insights in our culture and how we communicate being one of the largest, if not the largest remote company in the world are essential.”

Megan added that “here we have embraced Salesforce from a CRM perspective, but also deep documentation at a customer level and of our processes.”

“We document projects and processes internally. It’s not that hard to then adjust that content and make it available for customers. So I feel like we always have this huge head start on sharing our internal knowledge and capabilities with customers and prospects, which makes the job of our sales team selling remotely easier as well because there’s more self-service.”

Don talked about how his team leverages Gong, “as we onboard, we’ve got a library of calls that we’ve done that new reps can listen to and get up to speed.”

“In addition, we do analysis and pull out key words in conversation. That’s had some really cool impacts for us both from an outward-facing perspective. I find we’re taking snippets of conversations and inviting other people who weren’t there in that conversation to see what we talked about. It’s a way to keep those lines open and share, and keep continuity across conversations, things like that.”

Internal reviews help with training and alignment

In addition to informal chatting via tools like Slack, many of our panelists use some form of “stand ups” while working remotely. Jen said that Cockroach Labs does a weekly company call and then narrows down into each team.

“Everything is published, so if you want to sit on a call, you have the ability to do that to learn about what’s happening with a different team. We also record everything, and it’s accessible to the organization afterward.”

Something new Jen has added to the mix, though, is similar to an internal podcast.

“For example, you had a call, and the call went well. What was different about it? We do 15-minute vignettes of how did the cycle go, what were the things that you heard that were great or negative? Sharing more of how we’re sending out emails. What’s the message? How’s it changed? Who’s getting more opens?”

Here at Tackle, Don and the sales teams are taking a spin on the review process.

“My favorite new feature of my stand up call with my team, which we do on Fridays, is we created a blooper reel from all of our Gong sessions. So we’ve got the funniest moments. There’s always something that went a little sideways or whatever. It’s a great way to share some funny experiences, but also at the end of the day, you’re usually learning from somebody’s mistake, whether it’s your own or somebody else’s.”

Marketplace help sales teams do more deals, quickly

As many enterprise sales teams are adjusting to selling from afar, one way to accelerate transactions is to use Cloud Marketplaces.

Mayank noted that “when we first adopted the first Marketplace and did a health check and pulse check to see what the response would be, we actually began our journey with private offers almost exclusively. Deal acceleration was pretty evident. We already had a few deals that closed immediately. As soon as we launched in the Marketplace, we were able to transact in the Marketplace as well.”

Megan has also seen deals accelerated thanks to the Marketplace.

“Within a week of working with Tackle, we had made more progress than the previous five months and were very, very fast to Marketplace. Then once we had done that heavy lifting and understood our offering and what we’re trying to do in the first Marketplace, it was easier and much faster to get to market on the second Marketplace.”

Megan credits some of their success to relationships with Cloud providers.

“We have strategic alliances with Cloud providers. They are creating value for customers in searching for software applications and the procurement of those applications, and the ability in some cases to leverage third-party software costs to decrement, or to count towards a larger commitment to the Cloud provider on their consumption requirements for enterprise customers.”

For Megan’s company, the benefits of selling alongside Cloud providers play out in two ways.

“One is it just simplifies procurement at the basic level, especially with new customers.” When you leverage the Marketplace platform, you can often avoid lengthy contract negotiations to be set up as a new vendor.

“The second is being able to land and expand.” With extra budget available, renewals and expansion may be easier to complete via the Marketplace.

Jen noted that they’ve had a similar experience, “from Tackle helping us get into the Marketplaces quickly, as well as the customer interest in leveraging marketplaces as a purchasing vehicle.”

“The probably biggest addition I would make is engaging with the sales teams from the various Cloud vendors to help us get market validation relevant to our technology as a startup; that’s always helpful. But also, to help us and strategize on how do you get into these different customers in various ways leveraging the Cloud platform? That’s something that across all three Cloud platforms, we’ve seen some great engagement from the reps and helped us accelerate deals.”

All Marketplaces are not made equally

While the panelists have seen great success in selling via the Marketplace, the path isn’t always smooth. When we posed the question of what challenges they’ve encountered, there was a common theme around the differences in working with each Marketplace.

“I was going to say probably one of the biggest challenges is educating the sellers that every Marketplace operates differently. They think that they’ve got it down and they start the same conversation for a different Marketplace, yet the whole process is very different.” Jen shared.

“Understanding the value of selling on Marketplace has been a little bit easier, but the change, and the structure, and the flexibility, and the ability to negotiate is a little bit different depending on the Marketplace that you’re in.”

Mayank echoed Jen’s thoughts on the complexity of navigating multiple Marketplaces, stating that “all the Marketplaces are not made equally.”

He went on to note that “some of the technical difficulties are obviously some challenges. That’s where Tackle comes into play, obviously. Just top of mind, accommodating various different types of licensing models and pricing models can be tricky sometimes with a Marketplace, particularly if you’ve got a self-managed solution that you install and the customer manages.”

Finally, Megan added that tailoring deals and models to fit into the Marketplace setting can be tricky at first. “I think a challenge is the parameters of a Marketplace deal and how licensing pricing works, how that’s structured in each marketplace. Are you trying to fit a square peg into a round hole?”

“You’re trying to modify or come up with an offering that works well and is quite seamless in the Marketplace, but still has continuity across your whole offering stack outside of the Marketplace. I think that’s a challenge.” Megan shared.

For many sales teams, selling enterprise software remotely is a new challenge. If they want to thrive, there will have to be some adjustments. First, now is the perfect time to remember exactly what your product enables customers to achieve. Second, consider opening new communication channels or formats, such as office hours, to meet customer needs. You can also support your sales team through internal reviews, virtual training, and clear documentation.

Finally, leveraging Cloud Marketplaces can help you accelerate deals. Especially as your customers feel uncertain about the future, using existing Cloud relationships can lower barriers to sale. Just remember that each Cloud Marketplace operates differently, and your team may face a learning curve.

Want to hear more about selling enterprise software remotely? Watch the full webinar here.

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