6 Strategies to Move Enterprise Deals Forward in a Challenging Climate
Even in the best circumstances, the sales process is a balancing act that calls for careful timing, in-depth conversations, and a keen understanding of decision-making. In recent years, however, the process has become more complicated and prolonged, forcing sales teams to contend with new hurdles—from the rise of remote work and shrinking budgets to shifting priorities and technology platform consolidation.
As driving new business becomes increasingly complex, an expert’s guidance becomes more critical than ever. That’s why we spoke with Mike Fiascone, chief revenue officer and co-founder of Hundred Handshakes, a B2B SaaS account management platform that helps enterprise salespeople successfully expand their accounts. Drawing on over 25 years of experience in sales, Fiascone describes what sales teams can do to connect with C-suite executives and stay competitive in a challenging climate.
1. Find the right champion
The selling process stands a better chance of going full throttle when you secure a meeting with a critical company decision-maker, usually a C-suite representative such as the CIO or CFO. However, when these high-level executives receive as many as 400 unsolicited emails a week, success can hinge on your ability to first connect with a change agent a little lower down in the organization. It can take multiple attempts to locate and connect with a champion, but the payoff can be substantial. As an internal driver of the sales process, they can help open the door and build credibility with the C-suite executive responsible for buying decisions. Fiascone explained, “A champion is motivated to change, has access to power, and is willing to sell on your behalf, is moving, is taking action, is setting up the follow-up meeting, is checking in periodically. You have a texting relationship with this person.”
For small companies with few layers, your likely champion is the C-suite leader directly. But you’ll want to zero in on a vice president or director for larger firms, especially enterprises. Once you have your champion, there are two ways to climb the C-suite mountain. The first is the switch-back, bureaucratic trail. In a time-consuming but typical process, your champion introduces you to employees at different levels of an organization until you reach the top. The second approach is much faster but less common. When you know someone who is a trusted friend, board member, neighbor, investor, or advisor—and they have a close relationship with the C-suite decision maker—they can make a direct, warm introduction.
In both cases, you need to work with your champion to prepare a compelling sales pitch for your first C-suite meeting. “You have to arm them with collateral,” Fiascone said. “You have to prepare their presentation for them—with their branding. You have to use their templates and coach the champion on how to sell this inside of the C-suite.”
2. Don’t wait to feel prepared for C-suite talks
It’s natural for sales teams to want to prepare as much as they can before they meet with anyone in the C-suite. However, Fiascone warns that the fear of being underprepared can hold salespeople back from making crucial connections. “You’re never going to be completely ready,” he said. “The fear is a limiting belief—it keeps people stagnant.” Instead of waiting to gather more information and seeking perfection for C-suite conversations, sales representatives are better off booking a meeting as soon as there’s an opening rather than delaying a presentation.
In fact, having an upcoming meeting with a CFO, CIO, or other high-level leader can prove a compelling reason for mid-level employees at the prospect company to meet with you and ensure their voices are heard. This enables you to uncover valuable intel on use cases, current pain points, company strategy, division goals, and more.
3. Secure sponsorship for a strategic engagement
The goal of your first meeting with a C-suite executive should be to secure a strategic engagement lasting four to six weeks. This period allows your team to interview people throughout the company and answer the what, why, and how of the investment. You can also probe deeper into the use cases and pain points above and start strategizing on a deployment roadmap and cost-benefit analysis. For one insurance company, Fiascone’s team conducted 92 interviews across eight lines of business. This intense discovery period helped them identify 112 use cases, proving the business benefit they could provide.
Before beginning the process, however, it’s important to document everything you’ll do in the engagement period—from the meetings you’ll take and the deliverables you’ll prepare to your expectations and criteria for success. When the executive signs off on this plan, the clear expectation for all is that if your company meets these objectives and demonstrates the investment’s value, the prospect will commit to the purchase at the end of the engagement.
Once the strategic engagement concludes, sales teams should compile their findings in a report and present their data and insights in a follow-up meeting with the C-suite member. Fiascone explains, “The report isn’t so much about the product as the process and developing a recommendation and readout that tells the executive where and when to invest.”
Larger enterprises may take a phased approach to implementing a recommendation. But this shouldn’t be considered discouraging news if you present a provocative point of view to an executive ready to take action. Given the time and resources they’ve invested in the strategic engagement, they have a significant incentive to follow through with some degree of implementation. See Point 6 for more on how a phased implementation can lead to a more extensive scope.
4. Address security concerns early
Working on the contract terms of a developing deal before business discussions come to a close is an effective way to keep the sales process moving forward. As salespeople conduct conversations with executives, they should address early on contract terms that could stand in the way of the deal down the road—namely, security terms. He noted, “If they believe you can solve their problem, and if they believe you’re the right vendor, then pretty quickly I’d say, ‘Why don’t we have a discussion with security and operations while we work out the details of the business terms.’”
“You don’t want to spend six months working with someone, only to get to the end and have them say, ‘We can’t do business with this vendor. They don’t have the security controls. They’re not ISO 2700 certified; they’re not SOC 2 compliant,’” Fiascone explained.
Once you address all security concerns, you can move on to legal matters and a review from their legal team.
5. Overcome indecision by justifying immediate change
Sales teams may encounter hesitation and indecision when making their business case to company leaders. Overcoming these roadblocks requires asking the right questions and guiding the leader through the decision-making process. Ultimately, there are two vital questions sales teams must answer: why change and why now? While most people can be convinced of the need to change, the latter point is more difficult to justify. It must come from a feeling of urgency. Even ROI calculations cannot sway a person if they’re not motivated emotionally to change. This motivation comes from realizing the future impact of stagnancy, from lost revenue and outages to reputational damage.
In the face of hesitancy, salespeople must heighten the pain of stagnation and reduce the pain of change—emphasizing the problem, its impact, the ideal solution, the cost of inaction, and who’s affected. In essence, if this problem persists, how will you feel then? What are you going to tell your boss? "The biggest competition isn’t with other vendors," he continued, “the biggest competition is the status quo: staying the same.” By talking to senior executives, vice presidents, and mid-level employees throughout the company, you can bridge the gap between the leadership team and their employees and justify the need for immediate change.
If company valuations and market capitalization are at stake, executives will likely agree it’s a big issue that needs a solution. “You’ve got to get them to connect to the emotion of catastrophe: the worst-case scenario of the status quo. That will make them uncomfortable, but emotions drive people to take action—not logic.” Mike adds that appealing to the emotional side can be as simple as asking the prospect to envision their future state. He recommends prompts like, “How will it feel if it’s all automated? What we’re talking about can be deployed in just six weeks—why don’t you talk with one of our customers?” Suppose the answer is still no at the end of this process. In that case, your team’s resources may be better utilized by moving on to a different person at the company—or a different company altogether.
6. Select the right agreement timeline
In today’s apprehensive sales climate, some companies may be reluctant to commit to a multi-year sales agreement due to uncertainties about the future. That’s why new deals often have a one-year timeline, allowing the partnership to prove itself before the prospect commits to a longer agreement.
Multi-year deals have advantages, allowing buyers to lock in a fixed price and ease budget planning—a significant advantage in an inflationary environment. However, sales teams shouldn’t be disappointed with a one-year deal. This option can even prove ideal, as it forces the company to expand its relationship with the vendor within a relatively short timeline. Once you build a successful internal use case, you can push the implementation across the organization. “On larger accounts, you’re trying to make the landing as easy as possible. Make it a no-brainer to get your hands on the product and get it in your system,” Fiascone concluded.
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