For the Win: Closing the Deal in Startup Sales

So, you’ve met with a potential buyer, masterfully presented your demo, handled all of their objections like a pro– a deal close should be around the corner, right?

In a perfect world, yes, but the reality tends to be much different. Many salespeople and founders-turned-salespeople find themselves chasing a close too long, entertaining prospects that appear interested but don’t actually have intent to buy, and have trouble with getting a signature on the Docusign (dotted line).

The feeling of failing to close an otherwise closeable deal might seem as demoralizing as fumbling the ball at the 1-yard line. Still, it’s another opportunity to become a master of your craft and close more deals by iterating your sales approach.

The key to successfully closing out a deal is transparency between you and your prospect and understanding the sales levers available. Nail those, and more closes will be imminent.

Let’s walk through several closing strategies and tactics that you can implement at your company.

1.  Build the Close into Your Qualification Process

A flawless close often starts with a clear blueprint with build-in contingency plans during your qualification phase.

Once you’re clear on what a close-able prospect looks like, you can work on chiseling away at the many intricacies and cues of a close that would otherwise be lost in a larger quantity of prospects.

A clear checklist of objectives refined in your qualification process and later confirmed in your sales discussions will help you gauge whether a potential deal is moving to a close.

2.  Don’t Take Bad Shortcuts

Indifference, rather than errors in the sales process, is the reason roughly 65% of closeable deals fall through.

A much shorter sales cycle makes it easier to keep your prospects engaged while establishing an urgency behind your sales, but that doesn’t mean you should cut every corner possible.

Your prospects need to gather enough information and gain organizational buy-in before they can make a confident decision, and by haphazardly removing steps from your sales process, you run the risk of disrupting that process.

Break your sales process down into a series of step-by-step actions, and objectively assess the value-add of each step to uncover whether something can be omitted or combined with another step.

For example, if you cut a full demo meeting with a key stakeholder to save time, you may not have the necessary buy-in that would require a deal to close. Look for boosters, or ways to increase the velocity of a sale without sacrificing the quality.

Identify and optimize around the most momentous moments of your sales process that tend to push the sale forward. If there are any additional steps or time drains, such as a secondary demo for additional features, cut them and take note of how your sales process changes.

3.  Look for Boosters The Shorter Your Sales Cycle, the Higher Probability the Close

Anand Chopra-McGowan and his team have helped scale General Assembly from being a relatively small startup to millions in revenue from deals with companies like Walmart, Visa, GE, and L’Oreal by using sales boosters to keep the sales cycle as short as possible. A profile by First Round showcases a few of Chopra-McGowan’s booster tactics: 

  1. Requesting a follow-up meeting within 24 hours of the first meeting. This helps to cut days, and in some cases, weeks in review and communication lag.

  2. Send lean initial proposals for rapid feedback before fleshing out a full proposal. While a detailed proposal may seem like a sure-fire way to impress your prospects with your offerings, it often multiplies the time necessary for review. Make each proposal as low-effort as possible and open to input so that your final proposal is perfectly tailored to your prospect’s needs.

  3. Use preliminary 1-on-1 introduction calls to loop in any new members in large group calls. Salvage any group meeting time to focus on items that need multiple sign-off that would otherwise go to introductions. Taking just ten minutes to catch a new member up to speed can shave days of “we need time to sync as a team” lag.

  4. Follow up regularly for cancellations. Some enterprise meetings can take months to book, but by reaching out to the assistants of key stakeholders, you may be able to snag an opening.

4. Apply Pressure and Timeline Buy-in

Some sales cycles, particularly those for B2B startups selling to enterprise clients, can be incredibly sluggish taking up to 18 months to secure a deal.

However, there is a happy medium between applying pressure to keep momentum going and being too pushy.

By challenging and establishing how long each section of your sales process takes, you’ll give the prospect a chance to visualize next steps and how to prepare accordingly. Remember, you want to reduce as much friction and cognitive load as possible from the close. Streamline the process of getting a yes by including dialogue to structure next steps.

For example:

“Clients usually get back to us in about three business days if they have any questions or feedback, and we’re fairly quick to come back with a new proposal. If you get a chance to go through our deck today, we can touch base at 3:00PM EST as well.”

If your prospect’s assume a clear blue-sky to review sales material, they’ll likely take as much time as possible and sap the energy and momentum from your sales efforts. Avoid getting stuck in the follow-up rigamarole by touching base and agreeing on a potential timeline.

Timelines will vary depending on your particular organization, but once you break down your internal and external sales process, you’ll be able to send a prospect a general time table of what to expect.

5.  Ask for the Close - What Do You Say to Close a Sale?

If you feel you’re at the tail-end of your sales cycle but are still unsure whether there is any buying intent, it doesn’t hurt to ask for the close.

For example:

“Now that you’re familiar with what we do and how we can work together, it seems to me that this is a perfect fit. What are the steps we have to take to launch our partnership?”

Next, listen intently. If the prospect answers affirmatively and outlines their next steps (i.e., “I just need to get a sign-off from my partner”), you’re officially in the closing phases of the deal. If they answer with any ambiguity, you can gather two scenarios:

  1. You failed to probe for pain points, ask the correct questions, or present the right information throughout during the earlier phase of the deal. Ask clarifying questions like, “So I heard you say you were ready to move forward, what has changed?” Learn where you went wrong, iterate, and improve your process.

  2. The prospect doesn’t actually have any buying intent. If they made it this far past your flawless qualification and negotiation phases, and they still aren’t sure if they want your solution, then they likely didn’t have any buying intent in the first place. This happens, move onto the next prospect.

Keep in mind that closing a bad deal can often cost you more money than you make. Your deal closing process is a two-way qualifying process that determines if you’re both a mutual fit.

6. Look for Sticky Calls to Action

Is your company able to offer another non-monetary incentive to get the deal to close? If so, take full advantage of it.

Strategically establishing a need to act within a fixed timeframe changes the paradigm of the deal from “close when you want” to “if you don’t close now, you’ll miss out.”

For example, if your product is new, you can add an extra element of urgency by inviting prospects to your private beta:

“We’re super excited to potentially have you on board. I should let you know that you’ll have to make a decision by Thursday EoD because we’re launching our alpha next Friday – after that we’ll have to close sign-ups and I’d hate to miss you!”

Ultimatums, however, can be fairly tricky and should only be used if you have the utmost confidence that it will push a prospect to a close. By asking for the close in the previous step, you’ll have an idea of whether making a decision with a quick turnaround is actually within the range of reason for a prospect.

Final Thoughts

There’s no silver bullet to closing deals, regardless of their size – 74% of top closers surveyed by Saleshacker noted that they preferred a flexible closing process rather than a single step-by-step process.

Most deals also likely won’t close in a single call, so you must essentially be “closing” throughout your entire sales process. Closing happens over multiple touchpoints, interactions, many hours of work, and through a bevy of emotional swings.

By incorporating a few of the elements above into your sales cycle, you can boost both the speed and increase the likelihood of a close.