Chris Brubaker was the first finance hire at Poscript, a leader in SMS marketing (the texts you get nudging you to buy a cool hat that just went on sale, or reminding you about those sunglasses you left in your cart). He joined around $20M in ARR, taking over from a fractional accounting firm that was keeping the books straight for the co-founder/COO.

One of his first moves was building out a deal desk. While this sounds like a herculean task, he was actually the deal desk… one guy (who was also FP&A and Accounting).

Today their deal desk is much more robust, and includes an in-house commercial contracts attorney. But the overarching motivation was to bring consistency to establish pricing guardrails so they could be confident individual deal economics were durable.

Building a deal desk is more about establishing a process than growing a fiefdom of employees. Personally, I’d always slow rolled building a deal desk, thinking I’d be blowing up my G&A spend relative to benchmarks by doing so. But Chris coached me to think of it as more codifying a process than adding headcount (at least at the jump).

As Chris alludes to, deal desks are incredibly important when you start doing bigger deals with customers who are committing to increasing amounts of term and spend. Yes, you’re increasing revenue by a step function, but you’re also potentially signing yourself up for deals with poor unit economics that last more than a year. There’s both opportunity and risk.

In my seat-based SaaS experience, a deal desk becomes non-negotiable when you swim upstream to the enterprise and are doing deals over $100K in annual value. But I’ve observed you want to move even faster in getting your ducks (deals) in a row when your company relies on consumption or commitment based pricing, since the contracts can get whacky fast (and have a real cost impact to them). In Postscript’s case, managing per-message delivery fees and infrastructure costs are critical.

Chris was the deal desk for 2.5 years (the crawl).

When he hired his FP&A manager he started handing over some of the responsibilities to him (the walk).

And after another year of tag teaming the legal responsibilities with the help of an outsourced contract attorney, they exceeded the spend threshold to bring that effort in-house (the run).

The math for bringing an attorney in-house starts to make sense once you are spending ~1.5x outside what you would if that person was on payroll. I find that’s when having the tribal knowledge of individual deals is more important than the flexibility to turn the hourly spend up or down. It also creates a more consistent experience for reps who will interact with the attorney on a regular basis, while removing a lot of the coordination drag the finance team absorbs.

At Postscript, deal desk owns pricing, packaging, and contracting. They publish a rate card with clear boundaries. If a rep colors outside the lines, deal desk helps them repackage to make it work.

I asked Chris how they set pricing guardrails that don’t kill the momentum of a deal. He linked it to having a good idea of what the market they’re operating in is up to.

None of this is possible if the deal desk doesn’t stay close to their sales enablement team as well as the sales reps who are bringing in deals and hold the ground truths. It’s a virtuous feedback loop.

By being in the flow of a deal you understand the places you can push to keep margin high and where you need to give to keep win rates up.

To do so they factor in three different things:

If they can keep those three things in balance, they know they’re investing smartly without signing the company up for deals that will destroy value in the future.

To beat a dead horse on the macro: Chris and his deal desk team stay close to what their buyers are going through. While Postscript may be pricing competitively based on what other sellers are attempting to do deals at, if the macro shifts, everyone must adjust. As a software company that sells into ecommerce brands, this was very real when tariffs hit last year. While buyers are often liars (in his hilarious words) sometimes you can’t squeeze blood from a rock.

What gets a deal to “Yes” shifts over time.

Your COGS will change as the company matures (hopefully for the better, as you improve leverage in your operating model and supplier negotiations).

Competition also changes. While you don’t want to live looking over your shoulder, the reality is that most buyers are getting quotes from more than one company before signing. Depending on your competitive moats, some of this will impact the rate card.

And finally, the way you bundle your products changes. You either die as a single product company or live long enough to become a platform. If you get to the latter, you’ll want to incentivize adoption of multiple products, which alters the way you price a bundle. Multi product needs to therefore be contemplated in the rate card.

Postscript finds itself making small updates on a pretty regular basis, targeting 1x per year, but changing more often if the macro swings.

Deal desk, even more than the CFO, is often thought of as the Legion of “No”.

People don’t want to go to the deal desk just to get punched in the face.

So how do you design a deal desk experience that allows for reps to have a good chance of getting to yes, and also doesn’t create a time suck on the org?

If you set your guardrails so tight that reps are only talking to the deal desk when they’re probably going to say no, that’s not a great experience. You need to give enough room so finance can say yes 50% of the time. As Chris put it, AEs will be more open to talking to you if they have a coin flip of getting to a yes.

To take this a step further, you can automate a bunch of the stuff that a deal desk typically asks for. Chris vibe coded out a Slackbot that asks for the standard inputs they ask for.

It runs the calculations for that first layer, and is auto approved about 40% of the time it would usually go to deal desk. It’s auto denied 20% of the time. And 40% of the time it pulls in the humans. So reps get immediate feedback on 60% of deals. And it lets the finance team spend even more time on the 40% of deals that they know matter.

He used Cursor to build it in Python and connected it using the Slack API. Most of it is just math and simple UI. Chris jokes that you’d never put him on the infrastructure team at Postscript, but it’s a great example of something you can automate to make a more pleasant process.

The point of a deal desk is to do deals that make sense (not to purely block bad ones).

Sometimes as the CFO you feel like you’re the only one playing defense, while everyone else is pushing the ball down field.

A huge part of deal desk is education. But it is possible to preserve margin and move deals through the funnel. A big part of that is education. When you lead with the why (explaining how certain terms impact the business) reps start bringing you ideas, not just deals that require exceptions. Deal desks work best when they’re seen as revenue enablers, not hall monitors.

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