Before you blame the sales team, audit the support behind them.
by Robert Clinkenbeard, CEO of Wilson360
The second half of the year is when next year gets decided
End-of-season enhancement sales, snow contract commitments and the Q3/Q4 bidding cycles will help determine which companies make the shortlist for maintenance contracts starting in January 2027, and all of it will land in the next 120 days. Every owner and C-suite leader should be asking the same question: Is your sales and marketing strategy built to win that work, or are you sending your team into prime selling season under-equipped to compete?
I see this pattern often in my consulting work. Leadership sets sales targets, hands them to the team and sends them off with a single instruction: Go sell. What is missing is the support a salesperson needs to hit that number: current marketing collateral, a clearly defined Ideal Customer Profile, a CRM with usable pipelines and follow-up campaigns and structured sales training that includes role-playing real conversations with property managers and procurement teams.
Six months later, when sales are flat and targets are missed, leadership blames the sales team. Rarely does anyone in the C-suite ask the harder question: What did we fail to provide?
The data says this is a leadership problem
The research points to an uncomfortable truth for leadership. Organizations with formal sales enablement programs that include defined processes, useful content and ongoing training achieve win rates roughly 49% higher on forecasted deals than those without these programs. Companies with ongoing, structured sales training achieve about 22% higher quota attainment than those without it. One-time training events show minimal impact. The gains come from reinforcement, coaching and consistent practice over time. A pep talk at the winter kickoff meeting is not a sales training program.
Salesforce research shows reps spend only about 40% of their workweek selling. The rest disappears into administrative work, hunting for information and creating materials that should already exist. If your account managers are building proposals from scratch, tracking prospects in spreadsheets and improvising enhancement sales conversations, you don’t have a sales problem. You have a support problem.
What the toolkit actually looks like
For a landscape company preparing for the fall selling season, the required support is specific. Start with your Ideal Customer Profile. Which property types, contract sizes and client segments deliver your strongest margins and retention? Your team should be able to name them and, just as important, know which prospects to walk away from.
Next, look at your CRM. Owning the software is not enough. Your CRM needs defined pipelines for enhancement proposals, snow renewals and 2027 maintenance pursuits, along with follow-up campaigns for prospects who are not ready to sign today. Speed matters more than most owners realize. Responding to inbound interest within minutes, rather than days, significantly improves the likelihood of winning the work. A property manager comparing three bids remembers who responded first.
Marketing collateral should align with the season, including enhancement portfolios featuring before-and-after photos, snow response capability statements and safety and reliability documentation for RFPs. Your sales team also needs opportunities to practice. Role-playing renewal conversations, price increases and objections like “we’re happy with our current provider” helps average sellers become stronger ones.
Ask hard questions now
Before the fall rush, sit down with your leadership team and honestly audit the support behind your sales team. Does every seller know exactly who we are targeting and why? Is our CRM a working system or an expensive contact list? When did we last invest in real, repeated sales training rather than a one-off seminar? Can our team explain why a client should choose us in language that matters to them?
If the answers are uncomfortable, you have two options: Fix the gaps internally or bring in an outside expert to objectively challenge the current effort. Either way, address it now. The companies that show up to Q3 and Q4 with an equipped, supported sales team will own the 2027 shortlists. The ones who hand out targets and hope for results will have the same flat sales conversation next spring and will blame the wrong people for it.
Reprinted with permission. GIE Media. Lawn & Landscape August 2026 (c)
