The economy is settling into a new normal (at least this year’s version of normal) and after two years of rocketing sales, some newer salespeople are experiencing their first sales cyles that aren’t influenced by the recent funding boom. So how can sales leaders best manage their sales teams, both new and more experienced, to keep both morale and numbers up?

Stripe Sales Leader of Platform Partnerships Nicole Arboleda joined us at a recent Workshop Wednesday to share some tips. Workshop Wednesdays are held live every Wednesday at 10 a.m. PST for those of you who want to connect with SaaS experts.

Nicole has spent almost five years leading sales at Stripe. First, launching Stripe’s LatAm sales team, and now in the platform sales organization. She started her career cold-calling on a landline during a recession, so she still sees a lot of opportunity in the current environment.

You’ve certainly already observed that in the current economic slowdown, deal cycles get longer, new business gets tougher, and cross-selling and upselling into your existing customer base there increasingly more important deal cycles get longer, more scrutiny from more stakeholders. Every penny is measured and overturned. More parties are involved. Decision-making gets more opaque. And in general, you’re going to see more complexity and time getting introduced in closing deals.

Business gets tougher. There’s less general appetite for risk and change as budgets tighten. And then lastly, if you are in the position with the existing customers that you have that are loyal to you and know the value that you don’t already deliver today, ideally you’re able then to go into that customer base and think about expansion opportunities, either finding new units or organizations to cross-sell and upsell into or new products and services that they could benefit from too.

Bearing all of that in mind, there are a couple of things to keep top of mind. The first thing is that just like in high growth periods, down markets are slowdowns are also temporary. So we’re in a cycle. We don’t know exactly the length or can’t predict the length of the cycle.

But what we do know is that it won’t last forever. And when budgets tighten and there is more scrutiny, the cream does rise to the top and you’ll continue to win on value. And this is a really important point.

Customers are going to continue to ask for discounts. But our ability to continue to articulate the problems that we’re solving connected to the products and services and solutions that we provide and hold the line on value as much as possible is important to keep in mind.

Also remember that opportunity can be born out of trying times. Stripe was born out of the last recession, along with a number of other interesting companies that are still growing today.

You can’t control uncertainty, but you can create stability for your team. And the way that you communicate that is is incredibly important. This also applies to your customers and the market. It’s communicating empathy and value, and shifting the messaging you’re delivering to your customers, investing in customer relationships. We understand that there is the opportunity to go back where we’ve already won the one legal and procurement and gone through that process. They trust us to see the value.

It’s probably safe to say with high probability that the sellers on your team today are probably selling through a downturn for the first time and helping them understand how to anticipate the additional risks and anticipate the additional scrutiny, understand how to navigate the additional stakeholders that are now involved in a deal will be increasingly important.

And then the last piece is multithreading through an organization, but especially empowering the internal champion that your team is working with and making sure that that internal champion can be a voice to win the hearts and minds and continue to sell through an organization with you.

You can’t control the uncertainty, but you can create stability.

You want to create an environment where your team still feels like they can take risks, that they can be wrong sometimes, and that they can beat an environment where they’re continuing to try new things and be high-performing themselves. Nicole’s team has added a communication structure that’s been especially helpful. That structure is creating structure to ambiguity, and it falls into three parts. And so those three parts are communicating very clearly, very directly what you know, communicating very clearly and very directly, what you don’t know, but what you will know and win ideally. And then being really clear and transparent about the third thing here, which is what you don’t know. And going back and as you provide updates to the team, it creates a sense of stability around what is actually kind of a black hole or in the ambiguity.

As much as things might change around us, your ultimate goals and your missions will likely hold true. Keeping your goals and your targets clear and stable, and repeating that as often as possible is super helpful for the team to create that environment of stability.

Remind your team that the fundamentals aren’t changing. Your weekly team calls are a great time for this. Repetition breeds familiarity, and familiarity breeds confidence and trust.

This is similar to how you can approach customers as well. So when doubling revenue and growth becomes more uncertain, they’ll be focused on their bottom line on cost savings and operational efficiency.

It’s important to meet them where we imagine their mindset to be as well. So ideally you’re empathizing with the customer and importantly, communicating that directly as well and checking in with them as people and not just as prospects.

In an environment where you feel increased pressure and increased uncertainty, sometimes people react in ways that will reflect poorly on your company and work against your goals. So reminding the team to respond to customers empathetically is important.

When everything’s going really well, the messaging that they typically deliver at Stripe is, “Let’s talk about how other businesses like yours are working with Stripe to grow their top-line revenue.” As soon as they started to feel a shift in the market and how people were starting to respond to different actions in their own business, that messaging started to shift.

Now it’s, “So let’s talk about how businesses like yours are working with Stripe to save money and become more operationally efficient.” So meeting your customers where they are, reminding them that you understand where they’re coming from also, and then, of course, making sure that you have the product and services and solutions to deliver on those things. But the communication piece is probably the most important here.

The third piece here is investing in your customer relationships. This isn’t just about investing in expansion, cross-sell, and upsell. Instead of focusing the team only on growing revenue, it’s about reminding them and ideally having the structure on your team so that you’re not losing revenue in the first place from your existing revenue base.

You have to work with your team to retain your customers and their revenue, because they’re probably going to come and knock on your door even if they are happy customers, and ask for some discounts in some way or form. So first focus on retaining that customer, protecting the revenue you have today before it becomes a gap in your number, and then ideally above and beyond that, expanding into the install base.

The fourth piece is forecasting with more agility. As mentioned above, sellers are probably selling into a down market for the first time ever in their careers. And it’s been a great run that we’ve had. But helping folks understand how to anticipate that uncertainty in their own pipeline is going to be super important.

So be ready to dive in, be ready to help your team see around corners and articulate the risk themselves that may have not existed for them before. And importantly, welcome talking openly about the unforeseen risks on your team so that you’re ideally not creating blinders for your team or for others as to what the reality is of your funnel versus what we hope it is or what it used to be in a better market.

The last step is about, in turn, empowering your internal champion. We think a lot about multi-threading and so mapping, ideally, the executives and the different day-to-day operators within an organization or deal that you’re working on. And that is exceptionally important and will continue to be important.

Even with the best strategy and the best intention, you can anticipate getting blocked in certain ways. Knowing that and being ready for it is super important. Empowering your internal champion means ideally, you’re already texting with them. You have a really great relationship you built.

You know they understand the value in the business case, but it’s really about arming them so they can do the same as they go through their own organization that undoubtedly they’ll know better than yourself or your team. It’s even more important in this environment to ensure that the internal champion that you have within your partner organization has the assets, has the case studies, has the customer proof points, has the ability to articulate, and can speak to almost at heart the value that you’re providing that other customers can speak to as well.

It’s those customer proof points that are especially important in these times and that are emotionally helpful to make tough decisions these days. And then the second piece is, logically, they still need to make a decision. Likely every dollar spent in every deal is being more scrutinized.

So make sure that you have an airtight business case written down that potentially includes an ROI model that helps you to demonstrate the investment that they’re making in the partnership or in the motion that they’re thinking about today.

Remind your team that your internal champion is really going to be a key partner for you in these times.


  • You can’t control uncertainty, but you can create stability for the team.
  • Meet the customer (and market) where they are, and communicate empathy and value.
  • Invest in your existing customer relationships to retain revenue (your customers will be asking for discounts too) and expand strategically.
  • Forecast with more agility, anticipate more stakeholders, welcome, and be prepared for, additional scrutiny.
  • Empower your internal champion to multi-thread alongside you.




Every Wednesday at 10 a.m. PST, SaaStr will hold live, interactive workshops on Zoom where experts in the community share their insights. Sign up HERE!

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