The Art of the Deal: 8 Tactical Lessons for a High-Performing Deal Desk
The "Deal Desk"— a central hub that bridges gaps between sales, finance, operations, legal teams— shouldn’t just be a luxury for enterprise organizations.
All companies can benefit from a dedicated function supporting deal velocity, profitability, compliance, financial risk management, and customer satisfaction.
When well tuned, the deal desk improves operational efficiency, increases deal sizes, and increases win rates. But companies launching or growing a deal desk may struggle with where to focus.
In this guide, we’ll share eight lessons from experienced deal desk professionals. These leaders aren’t just armchair advisors; they’re in-the-trenches process architects who understand how to staff the shift from deal chaos to continuity.
Whether your deal desk team is non-existent, ramping up, or you are the deal desk – read on for ideas on how to build better.
Lesson #1: Know your purpose.
A surprising number of companies can’t define the purpose of their deal desk. Adding deal support is often the intent, but few can map this to specific business level activities.
Before standing up a deal desk function, confirm that an executive sponsor or champion vocalizes goals. “Have your champion promote these with leaders who will be the decision makers at a tactical level,” suggests Melissa Quinlan, VP of Accounting at LinkSquares.
Stakeholder teams may have priorities, but these must mesh into the described purpose–especially for small teams with limited resources and bandwidth. When the deal desk’s purpose is understood consistently (and widely), expanding the function becomes easier.
Lesson #2: At first, don’t change. Document.
Sales processes often originate organically. This means: No one knows exactly how the experience unfolds.
As companies grow and deal volumes swell, process definition gets lost in the shuffle. Closing deals becomes muscle memory–or “just the way we do things.”
“Companies need someone who understands what is happening from beginning to end,” guides Kathryn Shepard, Sr. Director Revenue Operations at LinkSquares.
A deal desk’s immediate value is discovering and documenting the full sales process – no matter how chaotic or refined. “Once defined, identify who is involved, and capture all handoff points, action steps, and required documentation,” shares Shepard.“This insight is a must-have for meaningful process improvement later on.”
Lesson #3: Break silos (before you break anything else!)
Improving deal flow depends on surfacing the business needs from every group that touches the quote-to-cash process. This behind the scenes work helps stakeholders feel seen and heard–essential ingredients for new process buy-in.
“Always start by asking questions,” suggests Ashlyn Donohue, Director of Legal at LinkSquares. “Dig up answers to what teams need to see, manage, or understand in the sales process to reduce risk. Also, clarify what bogs down a team in getting deals closed.”
Savvy deal desk operators know this requires probing beyond what teams would “like” to see in the sales process. Donohue suggests that these findings will make it easier to “sell” process revision.
“Uncover the genuine needs by exposing risks. For instance, what causes revenue recognition issues, commission inaccuracies, or unworkable customer commitments. Poor processes may allow these to slip through the cracks.”
Ashlyn Donohue, Director of Legal at LinkSquares
Lesson #4: Dream big, but start small.
Leadership experts warn against planning too big right away, while Harvard Business Review says that most high achievers are programmed to “go big or go home.”
The problem is, “big goals are more burdensome than they are motivational; they require daunting effort to accomplish and sustain in our busy lives.”
For many, regularly falling short of audacious goals may breed discouragement and deter future action.
Kathryn Shepard encourages new deal desk leaders to embrace a vision of versions; “You don’t need sexy, sophisticated systems right away. Figure out where you need to go now to catch issues or capitalize on your process priorities–and expect to iterate along the way.”
“Your first revision could be as simple as adding a notification trigger that sends a report to your finance team.”
The point is, you’ve established traction.
Attempting micro-improvements allows you the space to capture data, report, and change course. Plus, slowly introducing change is easier for teams who are reluctant to evolve.
“Try thinking about the future of the deal desk in phases: First, you bring awareness to what’s going on in the sale process. Then, you improve pace by reassessing approvals. Finally, you could move on to unblocking bigger bottlenecks or reducing risks with tactical shifts.
Melissa Quinlan, VP of Accounting at LinkSquares
Lesson #5: Perfect processes don’t exist.
Once the deal desk understands existing approaches and stakeholder priorities, it’s time to codify a sales process.
Processes will vary depending on product, industry, or company structure, but in general you should describe the journey (and handoffs) throughout key phases as:
- Quoting
- Contract creation
- Negotiation
- Order Execution
- Order Fulfillment
- Billing
- Revenue recognition
- Renewal processes
There are thousands of ways to describe sales workflows. What matters most is that deal desk creates a clear, repeatable, published process that gets results.
The hard part isn’t writing down a workflow, it’s getting everyone to comply. Make sure your process is comprehensive and easy-to-follow, and define KPIs and SLAs with stakeholder teams.
Just don’t let one-off scenarios keep you from publishing a process.
The occasional non-standard clauses or pricing deviation is bound to come up. But if you’ve been thorough, your sales team will know the prescribed pathway for escalation.
Lesson #6: Don’t wait for others, initiate improvement ideas.
High-functioning deal desks don’t wait for suggestions; they recommend improvements. But for suggestions to make an impact–whether you’re shortening protracted deal timelines or eliminating compliance risks–they must be grounded in data.
“Pick a target, whether monthly or quarterly, and look for activity patterns that impair the deal process,” suggests Donohue.
She notes how deal desk teams may notice spiking request volumes for certain contract clauses, or escalations for non-standard discounts or unique payments terms.
“If these don’t upset your risk tolerance, update your processes and allow reps to self-serve by enabling them to change certain clauses in the agreement using pre-approved options , or reassign approval authority to limit congestion.”
Just don’t assume stakeholders have this data or have the bandwidth to review trends. This is where the deal desk shines.
Lesson #7: Trust technology – but not too soon.
Resist the temptation to go all-in on technology right away.
Making things as automated as possible is a great long-term goal. But early on, temper your use of technology. Every new tool and step is a shift. You’re training new patterns and you don’t want teams frustrated with technological hiccups and reverting to old behaviors.
Pave the way for better participation by introducing doses of additive technology.
To start, consider the most high-impact areas for pairing processes with technology.
For instance, some revenue enablement practitioners emphasize the benefit of contract lifecycle management tools in the sales process. In many cases, the CLM easily supplements familiar CRM and collaboration workflows, unlocking benefits including:
- Building standardized contracts for easy self-service contract creation
- Quickly getting electronic signatures to close deals faster
- Digitally collaborating to manage negotiations and contract edits
- Automating contract approvals and forwarding
Sales and legal don’t often use the same tools– resulting in one-off communications or manual data movement during negotiation and contract review.
The right CLM and integrations eliminate this issue without requiring wholesale technology changes. Everyone gets to keep using the tools they’re familiar with, and instead of building a bridge between the two tools with manually reports or spreadsheets, deal desk uses smarter bridging technology.
Lesson #8: Add availability: office hours & AMAs.
Occasionally, eager reps circumvent sales process channels to get answers. One way to solve this is by proving deal desk’s availability. Some ambitious teams model this with published office hours and local team AMAs.
We’ve seen enterprises advertise 3x/week office hours with on-call team members available to support questions on in-flight opportunities.
If sales knows that deal desk is on deck at specific times, they may be less inclined to ping or email people directly when they bump into issues like quote approval acceleration or non-standard NDA review.
Separately, deal desk AMA's are an opportunity to serve up support on already scheduled sales team calls to handle issues in batches.
Use these conversations alongside process data to understand questions and improvement opportunities. “Otherwise, your upgrade efforts are a little bit of a finger to the wind. You don’t have rationale for why you do what you do,” says Donohue.
About LinkSquares.
LinkSquares helps legal department leaders drive innovation, reduce backlog, lower costs, increase revenue, and minimize loss. If you're ready to adopt the most effective solutions for the legal function—and harness cutting-edge artificial intelligence to improve every aspect of your department–then contact LinkSquares today.