CROs live their lives a quarter at a time. And just when you get done sprinting to the finish of one quarter, it’s time to reset the scoreboard and start all over.
Each new quarter is an opportunity to look back at what worked and what didn’t—and make adjustments as needed. Then you get to explain it to your reps, your peers and your board.
The Q1 to Q2 transition is a particularly interesting one in the sales year. Q1 is the time when we roll out all the big changes: comp plans, territories (or not) and new strategies. It’s exciting but also a little distracting. Q2, on the other hand, is all about executing.
As we head into the Q2 transition for 2025, I wanted to bring in some folks who know a thing or two about how to close out one quarter and kick off the next. I sat down with Ryan Burke and Steve Travaglini, two of my favorite sales leaders. Ryan’s the VP of Sales at Zilla Security (recently acquired by CyberArk). Steve’s the former CRO of LinkSquares who built the sales engine that powered them from $500k to $50M ARR. He’s now living that early stage life again as Founder and CEO of Winrate.
You can watch the interview right here on Substack but it’s also on YouTube if you’re into that. For those of you that prefer text, read on for some of the high points in the conversation.
On learning from the quarter
“Typically something jumps off the page that helps to illustrate, like this is actually a little bit different than the last quarter we experienced.” — Steve
Before you can go forward, you’ve go too look back and do a thorough diagnostic of the quarter that was. Steve emphasized win-loss analysis and stage-to-stage funnel conversion. Both need to be broken down by multiple dimensions: segment, vertical, buyer persona, rep and team (assuming your systems are actually tracking this stuff).
Once you’ve got all that, you need to compare it to previous quarters as a baseline. As Steve puts it, “the gold is in the variance.”
When Steve was at LinkSquares, their best conversion rates in 2022 were coming from CFOs, so they focused on that persona. Sadly, it didn’t last. ZIRP ended, SVB collapsed. Looking at the data in Q1 2023, it was clear something had changed. “Quarter over quarter, there was a fairly huge change in behavior,” Steve explains. That kind of shift is visible if you’re slicing by multiple dimensions and comparing the data across multiple periods (e.g. quarter over quarter and year over year to account for seasonality).
Quantitative analysis is important but you can’t rely on that alone. None of us have perfect data and the exact answer isn’t always available. Don’t forget how important it is to listen to your team—when the same issues bubble up repeatedly you know there’s a real problem.
Finally Both Steve and Ryan call out the need to combine data with your intuition. “Be data driven, but not data dependent,” says Ryan.
On pipeline coverage
“If you have to roll all sixes to hit your number, that's tough.” — Ryan
Shoutout, as always, to Dave Kellogg’s two questions:
Are we hitting the number?
Are we giving ourselves the chance to hit the number?
As we’ve discussed before, that second question is all about pipeline generation and pipeline coverage. Ryan’s pretty clear about how important this is: “I obsess over pipeline.” If you’re going into a quarter without enough pipeline, you’re not giving yourself a chance.
It’s important to look at the pipeline you’ve created in the current quarter to make sure you’ve got what you need for the next quarter. (While we didn’t end up discussing this in the interview, this means you need to really scrub your pipeline to be sure it’s real.)
It’s also important to look back at the pipeline coverage you had when you started the quarter vs where you actually ended up relative to plan. When it comes to determining if you’ve got “enough” pipeline coverage, that’s how you decide whether 3x pipeline coverage is really what you need.
Steve mentioned that they thought of their plan at LinkSquares in terms of “build” quarters and “close” quarters. While pipeline generation is an ongoing job, there are natural ebbs and flows during the sales year.
Ryan has an important call out here about recruiting. “Did we hit our talent goals?” he asks. You probably won’t hit your pipeline targets without enough ramped quota capacity.
On not fooling yourself
“The danger is that you're looking for some kind of alibi or a bias confirmation on a good quarter. And that's really not what you want to do.” — Ryan
The goal of breaking down the previous quarter is to truly understand what’s going on. Only then can you actually figure out what to do about it. As Ryan puts it, “You want to have a really good understanding of the inputs and the outputs and a good explanation for how is this machine working.” Otherwise, you’re just guessing.
That means avoiding cherry-picking evidence that fits a narrative. This can be tempting, especially if things aren’t going well. It’s easy to look for an alibi. Instead, ask first-principles questions about inputs vs. outputs. Verify them with your RevOps teams, your CFO and your managers to make sure you’re staying objective.
On communication
“Be transparent to your team. What's happening? Are you on plan? Are you off plan?” —Steve
Steve, in particular, had a lot of important things to share about communication with the team. Once you’ve done your homework on the previous quarter and made your choices about what to adjust, present that as transparently as possible to your team. Make sure you do it at all levels—from people managers to reps.
As with any communication, it’s important to manage complexity. As Ryan points out, you can’t expect to come back with a list of 12 things that need to change next quarter. Simplify it down to the most important ones and reinforce those.
No matter what, show up with data and explain how you’ll measure success. Steve keeps it simple: you can effectively drive change with “communication, transparency and measurement.”
On working with peers
“Sales is a team sport in the sense that it's the whole company. It's the output of what everyone in the company has been working on. And I think it's the job of the CRO to really help guide the whole organization on what needs to be done in order to affect that outcome.” — Ryan
Not everything that impacts sales is under a CRO’s control. Marketing, product and finance are all dependencies and they all have their own challenges to manage.
Both Ryan and Steve discuss how important it is to build strong cross-functional relationships where there’s trust and honest feedback. One way to do that is to make sure you’re bringing data to conversations—not just frustrations.
That goes for your team as well. Reps that are quick to point fingers at a product limitation, for example, don’t do anyone any good if they’re just griping and not helping to quantify the impact.
On the board meeting
“Every board meeting, they're just going to test you. They're going to throw something at you.” — Steve
I asked Ryan and Steve to share their advice for being successful in a board meeting—whether the quarter was good or bad.
Ryan stresses that you need a deep command of the metrics and an understanding of the “why” behind those metrics. When you have both, you can make a credible case to the board of how you plan to address any issues.
Steve talks about the importance of presenting a unified story with the other executives. “Do a dry run with your functional peers,” he says. He also shared maybe my favorite piece of advice: “do a big workout before the board meeting” so you don’t come in too hot. Sounds like Steve learned from experience on that one.
And more…
This was a super fun conversation. Watch the whole thing for a comparison of CRM data to cave paintings, at least one Richard Feynman reference and Steve’s Lebron-style photographic memory of quarters past.
Share this post