[4] Pivoting in Pumps: The Art of Adapting in Sales

Ever had to pivot quickly in heels? It’s all about staying grounded while changing direction—whether you’re dodging a sidewalk crack or saving a deal. Sales is no different: the ability to adapt, adjust, and stay balanced can make or break your success.

January, for example, hasn’t exactly been my runway moment. I’m at 80% of quota, but my prospects? They’re teetering on the edge of commitment, kicking the can further down the road. The solution? Pivoting—gracefully, of course.

The Importance of Adaptability in Sales

Keeping momentum alive in a sales cycle often requires a spark of creativity and an understanding of your prospect’s needs and priorities. By strategically leveraging industry trends, company milestones, and customer-specific deadlines, you can drive urgency and action. Here are some tried-and-true methods (with a twist) to keep deals moving:

1. Leverage Industry Trends and External Events

• Market Disruptions: When industries face regulatory changes, economic shifts, or competitive shake-ups, position your solution as the steadying force. Example: "The new data privacy regulations rolling out next quarter mean now’s the time to implement automated compliance. We can help ensure you're audit-ready before the deadline."
• Seasonal or Time-Bound Opportunities: Tie offers to seasonal trends. Example: "Start the year strong! Let’s build your compliance foundation now so your team can focus on scaling when Q2 picks up."
• Competitor Actions: Frame your solution as the superior choice when a competitor makes a splash. Example: "While [Competitor] offers X, we go a step further with Y—ensuring your compliance stays ahead of the curve."

2. Capitalize on Internal Company Milestones

• Product Launches or Upgrades: Highlight your latest features and exclusives. Example: "We’ve just launched Secureframe AI—tools designed to cut onboarding time in half. Let’s explore how that aligns with your goals."
• Limited-Time Offers: Create urgency by offering discounts, free services, or bundled packages. Example: "Sign by the end of January to lock in 2024 pricing and receive complimentary migration services."
• Exclusive Events or Webinars: Use educational events to position yourself as a trusted partner. Example: "Join our 'Building for SOC 2 in 2024' webinar—spots are limited, but I can reserve one for you."

3. Focus on Customer-Specific Deadlines and Needs

• Budget Cycles: Time your pitch around their fiscal calendar. Example: "With Q1 budget planning underway, now’s a great time to invest in tools that save time and resources."
• Project Deadlines: Show how you can be the hero for their tight schedules. Example: "We can implement your compliance framework in weeks, ensuring you're ready before your March initiative kicks off."
• Compliance Deadlines: Highlight the risk of inaction. Example: "With GDPR updates taking effect, we can streamline compliance so you're not caught unprepared."
• Personal Milestones: Tailor pitches to decision-makers’ goals. Example: "Congratulations on your new role! Let’s make your first compliance initiative a standout success."

4. Create Unique Compelling Events

• "Early Adopter Advantage": Offer exclusive pricing or perks for early movers. Example: "Be one of the first 10 customers to secure our new compliance dashboard and get a free upgrade package."
• "Compliance Countdown": Tie deadlines to critical compliance dates. Example: "Only 45 days left until your SOC 2 renewal deadline—let's ensure you’re prepared with automated testing."
• "Exclusive Industry Insights": Use data and insights to entice action. Example: "We’ve compiled benchmarks from companies in your industry—would you like a custom analysis of where you stand?"
• "Seasonal Savings": Align promotions with holidays or fiscal years. Example: "New Year, New Compliance Goals—enroll now to save 20% and kick off your 2024 compliance roadmap."

TL;DR: Creativity Fuels Momentum

Deals often stall because prospects lack urgency, not interest. By creatively framing opportunities, leveraging external and internal triggers, and aligning with their goals, you can reignite excitement and bring them to the finish line.

Remember: Every deal is unique, so customize these approaches to your audience. And just like pivoting in heels, a little finesse goes a long way! ??

Real-Life Pivot: January’s Slow Start

January is supposed to be all about fresh starts and big energy, right? So why does it feel like prospects have swapped resolutions for hibernation? Anyone else out there struggling to revive their pipeline after the holidays? I mean, ghosts are supposed to haunt us in October—but somehow, they’ve extended their stay into January!

Here’s the scenario: some of my most promising prospects have gone from “Let’s make this happen!” to “Let’s circle back in March.” It’s like they’ve collectively joined a witness protection program. Frustrating? Absolutely. But instead of pushing harder and risking burnout (or scaring them off completely), I’ve found it’s time to get creative and pivot.

And hey, if you’re feeling the January sales slump too, you’re not alone—let’s navigate the ghostly silence together!

• Re-engage with fresh value: Sometimes prospects need a little extra motivation to refocus. Offering something new and time-sensitive can reignite their interest.

• Create urgency with a limited-time incentive: "If you sign by the end of the month, we’ll include free migration services or an exclusive onboarding package to fast-track your success."
• Personalized solutions for their unique goals: "We’ve recently added automation for [specific tool or framework they use], which could save your team hours each week—perfect timing to start now."

In one case, reframing the conversation with a bundled migration offer at no cost if they signed by EOM worked like magic. Suddenly, the urgency clicked, and we were back on track.

• Shift the decision-maker’s perspective: When ROI feels abstract, bring it to life by addressing tangible pain points or costs.

• Focus on resource impact: "Your engineers are spending 20+ hours a month managing compliance tasks. With our automation, you can give that time back to your team for high-priority projects."
• Highlight cost of inaction: "Delaying implementation could mean more manual tasks piling up and a slower audit process. Let’s get ahead of that now."

For one hesitant prospect, I shifted the narrative to show how Secureframe could free up engineering resources, speaking directly to their biggest concern. That perspective pivot made all the difference.

• Celebrate small wins to build momentum: Not every deal needs to start with an all-in commitment. Offering a phased approach can reduce pressure and build trust.

• Suggest a pilot program: "Let’s test-drive the platform with a small framework or department to see how it fits your needs. We can expand as you see results."
• Highlight easy wins: "You’ll start seeing value within the first 30 days—automated compliance tasks alone could save 15+ hours for your team right away."

One prospect needed just a little push. By suggesting we start small and scale later, I removed the pressure of a large initial commitment, and now they’re seriously considering a pilot program.

Tips for Pivoting Mid-Deal

1. Read the room: Is the hesitation about budget, timing, or understanding value? Adapt your messaging to target those concerns.
2. Offer creative incentives: Think beyond discounts. Free migrations, added features, or exclusive perks tied to quick action can reignite interest.
3. Build urgency without pressure: Use storytelling and real-world examples to show the cost of inaction—while keeping the tone collaborative, not pushy.
4. Reframe objections: Turn “We’re not ready yet” into “Here’s how we can make this easier for you to start today.”

The Takeaway

At the end of the day, sales is about connecting with people—real humans who have their own priorities, challenges, and distractions beyond your solution. Every organization is different, and no two sales cycles look the same, but these tips are designed to remind you that a little creativity, empathy, and flexibility can go a long way when momentum stalls.

The key? Stay curious and engaged. Whether it’s reframing value, offering new incentives, or suggesting a phased approach, find ways to meet your prospects where they are—not just where you want them to be. And remember, January ghosts aren’t forever!

But I know I’m not the only one navigating slow months. What creative ways have you used to re-engage prospects or close deals when traction disappeared? I’d love to hear your tips, tricks, and success stories—or brainstorm together if you’re feeling stuck. Let’s keep the conversation going, share ideas, and help each other step into the next month with some fresh strategies. After all, sales is a team sport! ???