10 Strategic Priorities for a New Sales Leader in Your Landscaping Business

Whether you’ve just hired a new sales leader or stepped into the role yourself, the first 90 days are crucial. It’s not just about closing deals, it’s about setting up the right systems, aligning with operations, and creating a foundation for sustainable growth. This guide outlines the 10 key priorities for a new sales leader to focus on to drive impact.

📄 Want the full framework? Access the detailed strategic planning document.

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Sales Leadership in Landscaping Requires a Focused Strategy

Leading a sales team in the landscaping industry is fundamentally different from other sectors. It’s about building trust, solving real property challenges, and syncing closely with operations to deliver services on time and within budget.

Unlike other industries, landscaping sales are:

• Highly seasonal: Timing matters. Demand fluctuates with weather, municipal contracts, and property cycles.
• Service-driven: Each estimate must reflect real crew capacity, material availability, and client timelines.
• Relationship-based: Commercial clients, HOA boards, and property managers expect consistent communication and long-term value, not just a one-time sale.

That’s why a focused, strategic approach is essential. Without structure and alignment, even seasoned sales reps can struggle to gain traction.

Why the first 90 days are critical

The first 90 days are a strategic window to set the tone for how the sales function will operate. This is your opportunity to:

• Gain trust from your sales team, field crews, and leadership.
• Build repeatable systems instead of relying on individual effort.
• Uncover misalignments in how your company prices, positions, or delivers its services.
• Set measurable goals that guide performance and accountability.

Common mistakes new sales leaders make

It’s easy to get caught up in the day-to-day hustle. But these are the pitfalls that often derail new leaders:

• Jumping into proposals and pitches too early without understanding what your company excels at delivering.
• Failing to define an Ideal Customer Profile (ICP), which results in wasted effort on low-fit leads.
• Ignoring operational constraints, like crew schedules, material sourcing, and weather timelines.
• Treating sales as a siloed function, instead of integrating tightly with marketing, customer service, and leadership.

Avoiding these mistakes starts with strategic thinking and cross-functional collaboration.

The importance of cross-functional alignment

Sales leadership is about creating sustainable growth, which only happens when the entire organization is aligned. In landscaping, where crews, schedules, and seasonal demands all overlap, your ability to collaborate directly impacts your ability to deliver.

Here’s who you need to align with, and why:

• Operations: So estimates match capacity, and crews aren’t stretched beyond what’s realistic.
• Project Managers: To understand actual execution timelines and job site realities.
• Customer Success: To close the loop on client feedback, scope creep, and upsell opportunities.
• Founders and Leadership: To ensure sales goals drive the business forward, not sideways.

🎯 Sales alignment isn’t optional; it’s a growth lever.💬 Want guidance on how to build cross-functional alignment in your landscaping business? Join the free LeanScaper community for expert insights, templates, and direct feedback from other leaders navigating the same challenges.

#1 Understand the Service Offering and Market Landscape

Before a sales leader can drive growth, they need to deeply understand what the company sells and why it matters to customers. Landscaping businesses often offer a wide range of services, from lawn maintenance and seasonal cleanups to complex design-build projects and commercial snow removal. Each service has its own pricing structure, timeline, and ideal customer.

Where to start:

• Shadow your team. Spend time in the field with project managers, estimators, and sales reps to learn how services are scoped and sold.
• Map out your offerings. Break down each service by features, timelines, and margins.
• Study your competition. Identify what competing companies offer and where your team stands out.
• Craft your value proposition. Highlight what makes your company the best choice, whether that’s quality of work, pricing transparency, speed, or reliability.

🎯 Pro Tip: Your goal isn’t just to know what you sell, it’s to know why customers choose you over the competition.

📄 Want help documenting your unique selling points and aligning services to client needs? Access the strategic planning document.

#2 Identify Your ICP

Not every lead is worth pursuing. The best sales leaders know exactly who they’re targeting and why. The more clarity you have around your ICP, the more efficient your sales process becomes, and the more likely your proposals will resonate with the right audience.

What to do:

• Analyze past deals. Look at which clients have brought in the most revenue, had the fewest issues, or stayed with you the longest.
• Segment by service. Your ideal customer for maintenance contracts might be different than that for design-build.
• Collaborate with marketing. Use real sales data to refine ad targeting, email lists, and campaign strategy.

💬 Need help identifying high-value customers? Join the LeanScaper community to get tools and peer feedback for defining your ICP.

#3 Develop Your Sales Playbook

If every sales rep is doing their own thing, you’re leaving money on the table. A solid sales playbook brings consistency to your team’s approach while still allowing room for personalization. It empowers new hires to ramp up quickly and helps experienced reps close with confidence.

What to include:

• Tailored discovery questions: Guide conversations around common landscaping pain points: curb appeal, maintenance issues, seasonal prep, and more.
• Objection-handling tactics: Equip your team with responses for the most common client concerns: price, timing, contract commitment, etc.
• Upsell and cross-sell strategies: Turn basic contracts into multi-service clients by positioning add-ons like seasonal enhancements, irrigation installs, or mulch refreshes.

📚 A good playbook is a living document. Update it regularly as your market shifts and your team learns what works best.

📥 Want templates for building your playbook? Access our resource doc and check out peer examples in the LeanScaper community.

#4 Set Measurable Sales Goals and Key Performance Indicators (KPIs)

You can’t grow what you don’t track. Measurable, transparent KPIs help your team stay focused, create accountability, and give you a real-time snapshot of what’s working (and what’s not). Setting clear sales goals also ensures your team is aligned with leadership expectations.

Key metrics to define include:

• Revenue targets: Set monthly and quarterly goals broken down by service type.
• Deal size and close rate: Monitor how much each client is worth and how effectively your team converts leads.
• Upsell and cross-sell performance: Track how often your team expands the value of a deal.
• Lead-to-close conversion: Optimize your funnel by analyzing where prospects drop off.

🎯 Build a weekly dashboard to surface wins, red flags, and trends at a glance.
💸 Bonus Tip: Align KPIs with your commission structure to incentivize the right behaviors.

📈 Ready to build a high-performance sales dashboard? Access the LeanScaper playbook and planning document.

#5 Build and Optimize the Sales Process

A well-defined sales process streamlines your internal workflow and improves your client experience. From first contact to follow-up, every step should feel intentional, timely, and aligned with your brand’s professionalism.

What your process should include:

• Stage mapping: Clearly define what happens at each step (lead, estimate, proposal, and close).
• Standard operating procedures (SOPs): Create templates and workflows for common actions like site visits, quote delivery, and client onboarding.
• Client touchpoints: Schedule post-sale email or phone check-ins to confirm satisfaction and open the door for future work.

🛠 A great sales process reduces confusion, shortens sales cycles, and increases your close rate.

📥 Want to compare process templates and see how other landscapers manage sales? Join the LeanScaper community for tools and peer insights.

#6 Implement Customer Relationship Management (CRM) Software and Centralize Sales Data

Too many landscaping businesses operate off spreadsheets, scattered notes, and one person “just knowing” where every deal stands. That doesn’t scale. A CRM brings structure, automation, and visibility to your entire sales operation.

How to get started:

• Choose the right CRM. Look for one that integrates with your estimates, crew management, and marketing stack.
• Train your team. Ensure every rep knows how to update the pipeline, track tasks, and pull reports.
• Use the data. Monitor lead sources, close rates, response times, and pipeline value to uncover trends and gaps.

📊 Centralized data allows you to forecast with confidence, act on bottlenecks, and make smarter decisions quickly.

💬 Not sure which CRM fits your landscaping business? Connect with pros inside the LeanScaper community and get real feedback on what tools are working for others.

#7 Develop and Test Sales Pitches

A one-size-fits-all pitch doesn’t work in landscaping. Your clients range from busy homeowners to commercial property managers and HOA boards, all with different pain points and priorities. A strong sales leader crafts and tests messaging that speaks directly to each segment.

How to build pitch variations:

• Segment your messaging. Write pitch versions for residential maintenance, commercial landscaping, seasonal cleanup, snow removal, and design-build projects.
• Focus on ROI. Emphasize how your services save time, reduce long-term costs, or enhance curb appeal.
• Refine and iterate. Collect feedback from sales calls to improve tone, structure, and objection handling.

🎯 Your goal is to create a pitch library that reps can pull from, personalize, and refine over time.

📄 Need examples to start building your pitch deck? Download the sales leadership strategy doc and join the LeanScaper community to trade scripts and get live feedback.

#8 Create a Scalable Lead Generation Strategy

Great sales teams create predictable pipelines. That starts with a coordinated lead generation plan that blends marketing, outreach, and customer advocacy.

Your strategy should include:

• Collaboration with marketing: Launch SEO, Google Ads, and email campaigns that target your ICP.
• Seasonal and topical campaigns: Promote services like snow removal or spring cleanups when demand peaks.
• Referral and testimonial engines: Leverage happy clients to bring in more business.

🔁 Review and optimize your lead sources monthly. The best sales leaders don’t just fill the funnel, they track where deals actually come from.

📈 Looking for a proven lead generation template? Grab the full guide here and explore real examples in the LeanScaper community.

#9 Hire and Ramp Up the Right Sales Talent

Even the best strategy won’t work if the team can’t execute it. Building the right sales team means hiring for both cultural fit and industry know-how, then enabling those people to succeed fast.

How to build a high-impact sales team:

• Assess your current talent. Identify gaps in skills, experience, or motivation.
• Hire reps with landscaping or service industry backgrounds. Prioritize candidates who understand the seasonality and complexity of landscaping sales.
• Set 30-, 60-, and 90-day plans. Outline what success looks like for new hires at each ramp-up phase.

🧠 Pro Tip: Your onboarding process should cover CRM usage, playbook mastery, objection handling, and field ride-alongs.

👥 Want to see how other landscaping companies onboard new reps? Join the LeanScaper community for access to templates and team-building advice.

#10 Align with Operations and Company Leadership

Sales shouldn’t operate in a vacuum. In landscaping, alignment between departments is critical to avoid overpromising, underdelivering, or mismanaging resources. A strong sales leader acts as a bridge, ensuring the customer’s voice is heard while keeping the business grounded in reality.

Steps to foster alignment:

• Host bi-weekly syncs with operations. Review upcoming workload, crew availability, and capacity for new projects.
• Share customer feedback. Bring insights from lost deals, client objections, or post-sale conversations to refine service offerings and pricing.
• Ensure strategic alignment. Collaborate with founders and leadership to ensure sales targets support broader business goals, such as expanding into new services or geographic areas.

🤝 Sales success is only sustainable when the rest of the company is set up to support it.

📩 Want a proven meeting framework for cross-functional alignment? Download the full strategy document here.

Results You Can Expect from Prioritizing These Steps

When new sales leaders take a strategic, collaborative approach, the results speak for themselves. By building the right systems and aligning with key departments, your business benefits across the board:

✅ Stronger team performance: Clear expectations and consistent playbooks improve close rates and rep confidence.
✅ Shorter sales cycles: Streamlined processes move leads to closed deals more quickly.
✅ Improved customer retention: Better communication and delivery build long-term loyalty.
✅ Better alignment between departments: Sales, operations, and leadership all pulling in the same direction.

Join the Free LeanScaper Community Today

Implementing these strategies is easier when you’re not doing it alone. Inside the LeanScaper community, you’ll find:

📄 Free tools and templates like onboarding plans, KPI dashboards, and sales playbooks.
💬 Expert advice from other landscaping pros who’ve been in your shoes.
📥 Download the New Sales Leader Toolkit, a curated bundle of resources to help you hit the ground running.

👉 Join now and start building a stronger, smarter sales organization.

Frequently Asked Questions (FAQs)

1. How long should it take a new sales leader to get up to speed?

Most leaders should be fully ramped up by 90 days, with clear wins and team alignment by the end of that window.

2. What tools are best for CRM and pipeline management?

Look for CRMs that integrate well with your estimating and job costing tools. HubSpot, LMN CRM, and Jobber are strong options depending on your business size.

3. How often should you update your sales playbook?

Quarterly reviews are ideal, with updates based on rep feedback, win/loss analysis, and market changes.