The Touchpoint Tango: A sales cycle analysis

Posted April 19, 2024

Evan Klein headshot

By Evan Klein

VP, Product & Solutions Marketing at Outreach

It’s not your imagination. 

Sales cycles are getting longer.

Timeline graph showcasing the evolving sales cycle

Growth-at-any-cost has shifted to a profitable growth mentality. More can say “no” and fewer are willing to say “yes,” making negotiations even longer — and we have the data to prove it. Sales cycles are 21% longer with win rates 2% lower than in 2020.

The Outreach Sales Execution Platform serves millions of sales and revenue interactions  worldwide, so we turned to our internal database to understand how sales cycles and communication touch points have evolved, and what to do next to close deals faster, increase win rates, and communicate better. Warning: it’s a bit of a dance.

Sales cycle by deal size

Bigger, riskier, and less likely

Bigger purchases aren’t just taking longer, they’re riskier. After slashed budgets and mass layoffs, buying committees seem to be getting nervous, and want to be certain about their purchases. 

Deals below $10k were the only group to experience a year over year decrease in average days open and increase in win rate. The trepidation towards bigger deals and enthusiasm towards smaller deals indicates that even in the current market, buyers haven’t given up hope — they’re still longing for change. They’re willing to buy, but cost and risk have to be low enough to answer to their boards and bottom line.

But even in uncertain times, buyers are still looking for solutions to their business problems.

Sales cycle by industry

Not all industries are sold equally

Not all industries are experiencing the same squeeze, and these fluctuations are a reflection of the global financial psyche. Year over year, Finance and Insurance, in particular, shortened their sales cycles while increasing their win rates. This cautious market has buyers looking toward financial resilience.

Omnichannel data revealing that trust is still king

Omnichannel analysis: Trust is still king

This risk-aversion and comfort-seeking makes every sales  interaction even more valuable. Outreach supports every stage of a sales workflow, including communication channels. An omnichannel analysis has revealed that trust is still king. Relying on emails and calls won’t cut it in this market.

Quick communication can help your deal cycles speed up, but prolonged, meaningful contact (meetings) can increase your win rates. Now is the time to become a consultative seller, build familiarity, and be prepared to explain to and support your prospects. But sellers are going to need some coaching and guidance.

Data from Kaia, Outreach’s Conversational Intelligence software

Kaia, Outreach’s conversation intelligence tool, provides real time support during phone calls and video meetings, using AI to guide the conversation and remind sellers of important information. Outreach’s data indicates that using Kaia during a call moves deals 19% faster and boosts win rates by 41%, but this isn’t just a product declaration. This is a reminder that sellers need more training and better battle cards to confront current circumstances.

Multithread data indicating when more than one contact is engaged, deals are 37% more likely to close.


Everything is slower and less likely, buyers are anxious, and we’re all going to have to turn on our Zoom cameras. So, now what? We turned to Outreach Commercial Sales Manager, Michael Barker, for insight to navigate this market: 

5 essential strategies to thrive in today's sales climate

1. Buckle down and map your workflows

Take a look at your internal sales workflows to determine exactly where deals are slowing down and falling through. With a thorough analysis of your sales cycle and tech stack, you can adapt and power your processes for the current climate.

2. Prepare your teams

This market does not lend itself to intuitive selling. Based on your workflow analysis and call recordings, if available, establish coaching protocol to prepare your team. Freshen up your battlecards, conduct appropriate training, and review your tech stack to give your sellers (or yourself) the edge you’ll need.

3. Get personal & meet up

Don’t settle for the call, book the meeting. To build trust and encourage buyers, you’ll need to connect through meetings. “Use meetings to appeal to their humanity,” says Michael. “Help hand-hold your buyer and explain what steps are necessary to get the deal done, always leave every call with agreed-upon next steps for each side, and push for a calendar invite and meeting every time.”

4. Multithread, multithread, multithread

Use larger buying committees to your advantage, especially at the top. Outreach data indicates when more than one contact is engaged, deals are 37% more likely to close. But cross-department threading has the potential to increase win rates by 56%. “Aim for the highest part of the organization if you can,” recommends Michael. “The higher-up the  contact, the more likely you can get executive alignment and assuage any fears or uncertainty.”

5. Brace for greatness

The past year has been discouraging for sellers and this market has only gotten trickier. But successfully maneuvering these circumstances is about to seriously broaden and improve  your sales skills, so take on the challenge. “Remember that buyers are just people,” reminds Michael. “They want to get promoted, do a good job, and make sure their job isn’t at risk.” 

Quote from commercial sales manager Michael Barker, "Remember that buyers are just people. They want to get promoted, do a good job, and make sure their job isn't at-risk"
How Outreach can help

Outreach is the first and only Sales Execution Platform built for intelligent revenue workflows. Built on the world’s largest foundation of customer interactions and go-to-market team data, Outreach gives teams the tools they need to design, execute, and continuously improve a revenue strategy that is disciplined, achievable, and optimized for every stage of the customer journey — especially when sales cycles are longer than average.


Kaia: Outreach’s conversation intelligence tool guides and coaches reps in real time to help speed up deals.


Deal Health: Outreach’s Deal Health scores monitor and anticipate length and likelihood of a deal, while offering insights and actions to move deals along.


Forecasting: Outreach’s forecasting tool helps teams improve their forecast accuracy by 45%, crucial when planning and supporting deals.


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