Creating compelling events to drive urgency

Proven tactics for guiding deal timelines, overcoming inaction, and achieving sales success

DEAR STAGE 2: I am the first AE at a seed stage startup. We crossed the $1M ARR mark and have some great customer case studies, but I’m struggling to find a real compelling event to drive deals. When I look back at our lost deals, the #1 reason is “no decision” or “status quo.” I read your post about driving urgency a few weeks ago and am wondering if you have any ideas on ways to create a compelling event or deadline to help shorten the timeline to a decision? ~NAVIGATING EARLY-STAGE SALES

DEAR NAVIGATING EARLY-STAGE SALES: Psyched to hear that you read Josh Shaw’s 5 step process for driving urgency in a sales cycle! He shared some great ideas and wrapped up with the concept of a mutual action plan (aka building a shared timeline for a deal). Let’s double click on the need for a compelling event — there are some products and deals where that is natural, and others where it’s just not as obvious. 

To help me explore this topic, I tapped Sheela Zemlin of Bakkt, Bill.com, Taleo Oracle, and PwC (just to name a few) fame. Sheela has extensive experience leading sales teams of all sizes, and brainstormed a few ideas to put a structured timeline into a deal in the absence of an external compelling event. Read on…

Internal resource availability

For Enterprise deals in particular, there are often several internal teams that need to schedule and complete work to get a new customer up and running smoothly. Sharing that backlog/bandwidth/scheduling constraint can help guide a specific timeline by creating the feeling of scarcity.

While running Sales Operations & Strategy at Taleo, Sheela had a great vantage point from which to gauge capacity and availability of sales supporting teams including Solution Engineers, Professional Services and Training resources. She recalls “providing the sellers, and in turn, the prospects, with estimated lead times or a Gantt chart of a typical implementation timelines is often an effective, honest way to build urgency.”

To bring this to life, consider a large retailer planning to purchase and implement a cloud-based recruiting platform ahead of end-of-year seasonal hiring, where the typical implementation timeline is 3-4 months. If the timeline slips and they wait until the end of Q2 to purchase, it may mean they are understaffed during the critical holiday period leading to a significant missed revenue opportunity. By addressing these timelines early in the sales process, you can build a shared understanding of the sequencing of the deal and successful rollout to align with the customer’s key business objectives.

Negative consequences of inaction

Given the success you’ve shared with current customers, you are clearly running a thorough discovery process and identifying the customer’s biggest pain points and the challenges that led them to investigate potential solutions. Sheela’s advises returning to these fundamentals throughout the deal, “Revisiting and validating that this is still indeed a point of pain and helping to quantify the impact on the business (e.g., doing nothing and falling behind the competition, stalling 2 quarters and incurring unnecessary expenses from their current broken process, walking into the next board meeting with no update on their digital transformation of their financial operations due to a delayed buying process).”

It’s easy to focus on the positive benefits of a solution, but often there is value in identifying and discussing business risk. Sheela recommends walking together through the negative consequences of inaction. This approach can often become a catalyst for more immediate action.

Land and expand

Sheela shares, “My teams have often found success by simplifying the initial product purchase to one module instead of starting with the whole suite, or building early success with one department or location in the company before expanding.” In today’s macro environment, most purchases are going through some sort of committee or multi-layered review process. In Sheela’s experience, “the larger the prospect company and broader your product platform, the more decision makers are likely to be part of the equation. Committee decisions are never fast and important influencers are often missed in the account planning process. It may be easier for the company to bite off on a smaller price tag and footprint to start and could also be beneficial to your company to get early wins and champions on your side for the larger scale rollout.” As you think about this approach for your own company, consider if there is one team, product, or use case that has more obvious returns or lends itself more naturally to proving value quickly.

Purchase incentives

The “option of last resort” is to offer financial incentives (extended payment terms, product discounting or free periods) for deal signing by the end of the month or quarter. Sheela advises “These tactics put your company in a weak position in the negotiation process, may need to be offered more broadly if news spreads across the market or even your own sales team and of course may result in lower economics for your company.  However, there may be agreement amongst company leadership (e.g., CRO, CFO, CEO) that these risks are worth the potential additional sales within an important period.” It’s very hard to hold the line on these deadlines in practice — if you offer a 10% discount to sign by the end of the month and the deal slips to the following period, the prospect will in all likelihood come back with this ask again. 

Ultimately our role as sellers is to partner with our customers to deliver a solution that brings value either by solving a key challenge or opening up doors to a new opportunity. Compelling events are just one creative way to ensure we are marching towards the same timeline and goals. And remember, these are only effective if the compelling event has consequences for the customer — the fact that your EOQ is coming up, you have the deal in forecast or that this contract is the one that would get you over the line are of no consequence to your customer!  

We hope these ideas help as you head into the last month of the year. Happy selling and wishing your teams a strong close for 2023!

Until next week!