In 2016, Jesse Rabbits passed his bar exam and finished law school. He quickly realized he’d never be happy wearing a suit and sitting at a law firm. The money just wasn’t worth the lifestyle for him.

So, like most people in the industry, Jesse found his way into tech. He worked his way up the ladder, first at Namely as a Support Specialist to GitLab as a Senior Deal Desk Analyst.

Now a Senior Deal Desk Manager at GitLab, Jesse works on enabling his team and internal customers to close deals faster, more efficiently, and more valuably.

His transition from entertainment to law to deal desk rested on his ability to forge fruitful relationships. Over a wending career from entertainment to law and now sales, Jesse has collected years of experience closing complex deals and managing teams.

Joining us from his home in New York, Jesse shared his thoughts on deal enablement, sales documentation, and deal desk leadership.

How to build a deal desk team from scratch

In a deal desk role, curiosity is an edge. When Jesse became a Contract Manager at Namely, his work involved close collaboration with its sales team.

Over time, he came to learn their needs, processes, and problems — and noticed several gaps. However, there was nobody responsible for plugging those gaps at the time.

Namely’s Head of Legal eventually approached Jesse to build the first deal desk team at the company, responsible for deal enablement and acceleration.

“I had never heard of a Deal Desk, but I tend to listen very closely to the stage directions the universe sends me. This was a chance to forge a new path - something unique - and someone I knew and respected thought I had the chops to make it happen. And so that’s what I did.” — JR

From a deal desk perspective, many of Jesse’s priorities are enablement, information sharing, process documentation, and efficiency — all aiming to make processes clear to GitLab’s employees across the globe.

3 essential tips to improve deal desk

Deal desk success depends on a strong offering, aligned values, and metrics.

A strong offering is key

Your sales team is only as strong as your product. A solid product with clear benefits makes for easier marketing, more demo requests, more retention, and less churn.

A poor product delivers higher CAC relative to LTV, more churn, and a harder time maintaining organic growth through word of mouth.

The rest, says Jesse, is mere logistics, and the logistics of how to deliver a product and its benefits into a customer’s hands will vary from company to company.

Align your values

At GitLab, Jesse leads a deal desk team of 13 deal desk and order management professionals. He focuses heavily on value alignment in his role.

“As a Deal Desk leader, I’m focused on keeping our Sales processes in line with our values: Creating space for collaboration, focusing on results and efficiency, and maintaining inclusion, iteration, and transparency.” — JR

Track your metrics

Another thing Jesse focuses on is metrics. As a deal desk leader, he is responsible for tracking trends in sales numbers across regions, customer segments, and products.

But he also tracks his team’s performance to ensure they’re hitting their goals without undue blockers. This iteration is key to keeping up with the needs of both sales reps and customers.

“On any given day, I’m looking at KPIs. What types of deals are coming from which regions? What opportunities do we have to enable our sellers to be more efficient and self-serve? How long are approvals taking, and why?” — JR

You could describe deal structures as puzzles — an attempt by sales teams to meet customers’ needs while adhering to standard sales operating procedures, remaining compliant, and maximizing value for both parties.

Build self-service into deal desk processes

Think of a deal desk as a SWAT team. They complete special operations (complex sales) that can’t be handled by standard law enforcement (sales teams).

But while SWAT teams are effective at their jobs, they’re not meant to be a permanent solution to crime. Instead, their learnings are meant to help law enforcement teams around the country to fight crime better.

Likewise, deal desk teams aren’t meant to handle every complex deal but to empower sales teams to solve more of those deals over time.

Jesse applies this self-service philosophy to his team and GitLab’s customers, choosing at every turn to enable them along their journey — or, as he calls it, to “teach them how to fish.”

For starters, the easiest customers to deal with are those that self-serve your product. This reduces or removes the need for complex sales motions to educate or onboard the customer.

Achieving this, however, requires an investment in ongoing demand generation and sales enablement collateral. These investments ensure that customers can self-educate during their consideration phase and raise their hand primed to buy.

Hint: ungating content speeds up this process and reduces friction.

The self-serve philosophy also extends to Jesse’s sales reps and deal desk professionals via sales documentation.

This involves creating a playbook for sales reps that answers any questions they might have when navigating complex sales. This, in turn, reduces sales cycle times and increases efficiency.

“At GitLab, many of our processes are available in our public handbook. The handbook is the ultimate process guide for our Sales org — a “home page” for the “how-to” questions.” — JR

Leading a deal desk team remotely

The pandemic distributed sales teams and introduced challenges around team management for many managers.

Jesse advises other deal desk leaders to emphasize communication, documentation, and iteration to overcome these challenges.

At GitLab, teams emphasize asynchronous communication — delayed comms caused by time lags or time zone differences where people don’t have to be present simultaneously. GitLab’s handbook has over 2,000 web pages to support its global teams.

“Process changes, operational changes, anything relevant to the Sales process — it’s all communicated widely, transparently, and asynchronously. Doing so enables our team members to work autonomously and efficiently — and it’s more inclusive.” — JR

5 tips for building a career in deal desk

Advancing into deal desk leadership requires certain mindsets and approaches to sales. Jesse shares his top five pieces of advice:

1. Invest in tools early
2. Master quote to cash
3. Be more humble
4. Hire for passion
5. Be kind

Invest in tools early

Classic sales advice implores you to focus on the fundamentals and not get distracted by shiny new tools. But Jesse implores sales leaders to invest in sales tools early.

Your CRM, CPQ, and other tools must be robust and structured to create guardrails for your sales team.

“Don’t lean on manual, human-led processes for longer than you must. The longer you wait to pivot to automation and software that adds value, the harder it is to re-train a Sales team who are used to humans doing everything for you.” — JR

Master quote-to-cash

One such transition deal desk leaders should make is moving from Excel to a CPQ tool. Configuring, pricing, and quoting products and services are core aspects of deal desk management. As Jesse advances his career, he leans more toward quote-to-cash processes.

This aspect of his job helps him understand revenue recognition from an operations perspective, critical financial planning and analysis elements, and how deals impact commissions and compensation.

“The more I learn, the more questions I have. The deal desk is one piece of a much larger puzzle, and I find it fascinating to learn the other elements of that puzzle.” — JR

Be more humble

That fascination with learning is a function of humility — probably the most crucial quality of any sales leader.

Part of deal desk management involves being decisive and direct, but collaboration is vital to solving problems.

Recognizing the talent on your team — and the fact that you hired them in the first place for that — helps keep things in perspective.

“I don’t ever want to be in a position where my decision makes someone’s day harder, and they had no say in the matter. Those folks know a lot that I don’t know, and I want to learn from them.” — JR

Hire for passion

Passionate people focus on possibilities, not limitations. Candidates who care about what they do and have a defined perspective make for better teammates.

“I look for candidates who have perspective and care about what they’re doing: work, school, hobbies, pets, or family. I look for a certain energy that tells me that they’ll take whatever they spend their time on seriously.” — JR

Apathy shows in how one approaches the job and how they treat customers and other team members. Apathetic people are also more likely never to challenge anything, leading to limited innovation and improvement.

Be kind

Kindness improves relationships. People struggle with different things in the workplace — teammates, tasks, and tools — and outside of it, like family, health, and death.

Showing empathy and grace builds long-lasting relationships while allowing people to bring their best selves to work — even during challenging days.

“Being kind and building genuine relationships improves the quality of life for anyone in a sales role. I like to remind folks — “At the end of the day, we’re just selling software.”” — JR

Looking back, forging forward

Jesse is adamant he’d do it all again — go to law school, get his license, and still pivot to the deal desk.

“The legal frameworks I learned helped me immensely in Deal Desk roles. They’re translatable and make you more confident when handling make-or-break deals.” — JR

To him, tech is more exciting and gives one the feeling of working on something bigger than oneself. And he wouldn’t have it any other way.

Connect with Jesse Rabbits on LinkedIn, and return for another story from Sid Sharma, Head of Sales at SaaS Labs, on how to nail your international go-to-market strategy.

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