How do you get the Csuite team to buy into a new pitch deck?

If I was an exec at your company, I’d want to understand what is awful about this pitch (share research, client feedback?), what evidence you can provide that it is hurting my business (do an a/b pilot?), and what you think good looks like (comparative/competitive examples?). If you brought that to me, I’d hope I would listen. Then, if I was you I’d try to listen really carefully to what this executive is worried about. Bad timing, overwhelmed sales team, something else? Maybe you can then address those concerns more directly.

Dig into the pitch and do the research to back it up. Gather feedback from reps (and customers, if possible), and communicate a direct correlation to how it is hurting sales opportunities. Is it the pitch deck or is it poor pitches? If you have an enablement partner, can they shed light as well? At the very least, even if the pitch decks and pitch training does not get a full overhaul for whatever reasons your exec team communicates, if you are able to get your stakeholders to act on a few discrete/incremental improvements that lead to positive sales outputs, you will have had a quick win under your belt that sets you up for future credibility with execs.

In these types of situations, I’ve found that data can be a useful persuasion tool, because it’s objective. Have you considered surfacing win rate numbers? Or an even more granular metric in the sales funnel, like a lack of deal progression from early to mid/late stages?

If execs are expected to take you at your word that the pitch isn’t working, based on anecdotal evidence, that can be a tough sell. Their thought process is likely, “how bad could it be? We’re doing well enough to merit an IPO.”

But if the data is on your side (which I’m sure it is!), it may be obvious that there’s nothing to lose by changing things up.

One trick that’s worked for me, whether I’m working off of data or a hunch, is to run an experiment with a small group of sales reps. If they aren’t winning deals, they aren’t making money, so they’ll be receptive to trying new things. Workshop a new deck with them and then have them use it during sales calls. If it works, you’ve found more people to support you in the case for change. You’ve also de-risked a broader rollout of a new deck. It sounds like you already have a pilot in motion, which is a great start.

Bad content is so frustrating! I generally use one or all of these tactics when I’m facing headwinds like this:

1. Try to understand the cause. It sounds like what's behind the c-suite pushback is fear of change, and in my experience, CxOs (like the rest of us!) sometimes just need to be reassured that everything will be fine. You can help everyone feel better about trying something new with a little social proof (e.g. at most software companies, the corporate pitch gets a refresh every 3-6 months) and with a solid Plan B (if the new pitch bombs, you can always go back to the old one).
2. Build a coalition. If you can find some good cross-functional allies who agree with you, you can each build support within your respective teams/networks. It sounds like you have some good allies in the sales team (if they know they’re losing deals due to poor pitches, they’re probably motivated to fix that). Look to other teams, too, so you can start winning over the c-suite one by one.
3. Take the pilot approach. You don’t have to roll out a change to everyone in the company immediately; it can feel less scary if you pilot it with a small group (in your case, maybe just one sales territory or account segment), show success, and then gradually scale it out.

First off, great job on finding a problem and bringing people together to fix it!

I'd suggest having a little bit more curiosity and empathy around why the CSuite members are hesitant. I'm guessing there might be more going around the IPO and that there isn't actually a desire to be "consistently bad." In situations where I feel like things are non-sensical I try to pause and listen harder to see what isn't being said.

In terms of selling the new pitch decks, I'd suggest positioning it as a "pilot" or "experimentation." It immediately drops the pressure around wholesale adoption of a new method, lets you move forward, and gives you the data you need to prove your hypothesis. If the pitch decks work fantastically, even if you only have anecdotal evidence, you may end up convincing everyone to adopt the new ones! Never underestimate the power of a few sales team members, or your Head of Sales, advocating for change. 

There are already a few good answers here, but no one has mentioned jumping on the impending IPO - what's the pitch for that? There should be a story followed by great metrics. The story for an IPO shouldn't be divorced from the customer pain and adoption the company solves. 

Also, on the pilots - find some reps who are respected, but not in the top 5%. You want people who want your help, but not the ones selling on years of knowledge and relationships. You also don't want reps in the bottom 50% - they want your help, but the likelihood they get cut is high. The thing to do with the top 5% is to find out what they are using and doing - especially if they aren't using the standard-issue materials.