Killing your own deal cycle

The sales team has received good news. You’re a finalist and have earned the right to propose. You now have the green light to quote and proposel. The party is on! But then you hear that record scratch.

Boom. Roadblock. You have to go through pricing committee. You have to get approvals. You positioned the sale wrong and it doesn’t align to your price book. You verbally discussed payment terms that finance wouldn’t approve. You sent out an agreement before legal could review it.

You thought you worked at a lean, mean enterprise but now you feel frustrated because this feels BUREAUCRATIC

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How this impacts the sales cycle

Often times folks can blame slow sales cycles on rep performance instead of internal process friction. Why do sales cycles take 300 days? Yet some reps bring in similarly sized deals in 200 days? In these cases I always think it’s best to break down the anatomy of a sales motion.

It’s not always the rep, it’s the system.

The sales motion may look something like this:

• Discovery & Awareness (Day 0–60)

• Problem Framing & Internal Alignment (Day 60–120)

• Solution Design & Evaluation (Day 120–200)

• Negotiation & Business Case Development (Day 200–260)

• Final Sign-Off & Procurement Close (Day 290–300+)

But somewhere along the way internal delays may occur and stall the deal. A quick deal inspection with reps is always good to go through. If you have MEDDICC in your org I’d highly recommend calibrating 1:1 sessions to identify if any of these symptoms are afoot.

• Re-orgs or budget shifts: Changing priorities can stall or reset the deal

• Champions leave: Momentum can be lost entirely

• Vendor (our own) missteps: Poor follow-up or slow responsiveness can add weeks

• Time-consuming factors:

  • External vendor issues (compliance, references, etc.)

  • Internal misalignment resurfaces

  • “Ghosting” from key decision-makers

No deal is the same as the other, but they definitely rhyme. Great sellers surface these issues early and use the processes and systems around them to their advantage. In some cases, it’s best to parallel track these workstreams. This saves time.

Don’t necessarily wait to do both the 1/ business ROI assessment and 2/ technical validation in sequence. Do it in parallel.

Don’t wait to align internal stakeholders on pricing, positioning, and terms before proposing. Do it in parallel or early.

Don’t wait to align CSM resources to an account you’re forecasting as a commit. Do it in parallel or early.

This is what can shave time on sales cycles. And guess what, it’s not one seller doing everything. It’s a team event.

The tools to help you succeed

Knowing this, here are a few tools that will help you:

• Product and Pricing sheets

• Quarterly offsite trainings on the company’s offerings

• Deal Desk. Two flavors:

  • Proactive

  • Reactive

• Alignment w/ InfoSec, Legal, and Finance on end of quarter forecast

• CPQ tool

I’ll go into each one in detail.

1. Product & Pricing Sheets

These are documents that could be dynamic and regularly updated. Most likely you’re updating them once or twice a year. But they should include packaged offerings, upgrade paths, and typical deal structures. The sales team references these documents to identify what they can and cannot do. What is inbounds and what is out of bounds. If it’s out of bounds, then it submits the deal or better yet triggers deal desk (more on this in a second).

2. Quarterly GTM Enablement

Every quarter the team meets together for a few days of training and updates. Ideally you’re doing a deep dive on new features, pricing changes, and competitive intel. Quarterly sales meetings should definitely have Product Managers attend. At least that is what I’ve seen high performing organizations do. This should help sellers drive faster positioning decisions with less back-and-forth. Bring in both Product and Marketing. Sales will learn a lot from having those different perspectives in the room.

3. Deal Desk: Proactive + Reactive

There are two flavors of deal desk: proactive and reactive. The most common is reactive. You’ll know you have a reactive org when you:

• Find out a deal has odd terms that know one vetted before the prospect or customer saw it

• RevOps or Finance is asked to key in non-conforming details into your CPQ

• Legal pushes back heavily at the 11th hour on a critical deal because they have not seen the contract well ahead of time

Credit to Scratchpad for the meme!

The reactive Deal Desk function responds to requests when things go off-path (redlines, last-minute pricing help.

The flip side, and more rare setup, of this is the proactive deal desk. They’re brought in on strategic deals early to craft win-win deal structures. They’re advisors and not having to deal with “deal cleanup on Aisle 6!”

4. Cross-functional Forecast Alignment

Legal, Finance, and InfoSec review projected deals in commit. They know about the deals coming down the pipe. These organizations have other priorities throughout the quarter. When sales barges in and screams that their deals take precedence it creates stress on these orgs. That’s not partnership! That’s bullying.

Ideally we don’t have bottlenecks because we highlight these deals in advance. Each of these functions carves out time to be heads down on deal support.

If you’ve seen that contracts take an average of four redline rounds and each round takes 4 business days, then you’re looking at 16 business days or 3.2 calendar weeks. Do NOT submit contracts with 15 days to spare in the quarter. It’s just not going to pencil.

5. Modern CPQ Tools

Last but not least, is to have a CPQ system that works for you. CPQ projects have never been my favorite. They often take multiple quarters and one or two full time resources. Plus, some CPQ systems are a one-sized-fits-all and do not support multiple GTM motions (e.g., usage-based, seat-based, hybrid).

Here are 13 requirements I might suggest. Paid members have access to the requirements template as well.

1. Product & Bundle Configuration

• Support for multiple product types: subscription, usage-based, perpetual, services

• Dynamic bundling (rules-based or guided selling)

• Add-on/up-sell/cross-sell recommendations

• Rules-based configuration validation (e.g., “if X is selected, disable Y”)

2. Pricing & Discounting

• Tiered pricing (volume or user-based)

• Custom pricing logic (e.g., geography, segment, partner)

• Discount thresholds with approval logic

• Multi-currency and exchange rate support

3. Quote Generation

• Branded quote templates (PDF, digital signature-ready)

• Auto-population of customer and product data

• Quote versioning and audit trail

• E-signature integration (e.g., DocuSign, Adobe Sign)

4. Approval Workflow Engine

• Dynamic routing (based on discount %, margin, deal size, etc.)

• Support for sequential and parallel approval chains

• SLA reminders and escalation rules

5. Policy Enforcement

• Guardrails for deal desk (e.g., minimum margin enforcement)

• Business rules for product compatibility and pricing constraints

• Built-in checks to block invalid combinations

6. Multi-GTM Motion Support

• Direct sales, channel, product-led growth (PLG), usage-based, etc.

• Role-based configuration (AE vs Partner Manager vs CSM)

• Support for both simple and complex deals (enterprise, expansion, etc.)

7. Collaboration Features

• Internal notes and comments on quotes

• Tagging or assignment to deal desk/legal

• Notifications for status changes (approval, signed, etc.)

8. No/Low-Code Admin Interface

• Rule and workflow management without developer involvement

• Easy-to-update product/pricing catalogs

• Sandbox/test environments for QA

9. CRM & ERP Integration

• Native sync with Salesforce, HubSpot, Microsoft Dynamics

• Push/pull quote and product data to/from ERP (e.g., NetSuite, SAP)

• Bi-directional sync of deal stage, pricing, and closed-won status

10. Data & Reporting

• Pipeline visibility by quote stage

• Win-rate by pricing tier, product bundle, rep

• Quote turnaround time metrics

11. Scalability & Performance

• Handle large product catalogs with fast load times

• Support global teams and distributed selling

12. Security & Compliance

• Role-based permissions

• SOC2, GDPR, and ISO compliance

• Audit logs for compliance reviews

13. AI & Automation-Ready

• AI-driven discount recommendations

• Quote suggestions based on historical deal patterns

• Automated renewal or expansion quote generation

Templates you can use: