The Sales Leader’s 2026 Playbook: Planning, Hiring, and Crushing Targets

Planning season is here, and it’s your moment to set the tone for 2026. On the Growth Department podcast, Chelsey Reynolds sat down with Steve Levitt, a former CRO turned operator-recruiter, to unpack how great sales leaders plan ahead, hire smarter, and scale teams that deliver consistent results.

Steve has lived it all: building teams, designing comp plans, recruiting for hyper-growth companies, and cleaning up the chaos left by poor planning. His message is simple and direct: start earlier, get clearer, and lead with consistency.

Listen to the Full Episode on Apple, Spotify, and watch on YouTube.

Why Planning Season Starts Earlier Than You Think

Most companies wait too long. By the time January arrives, hiring pipelines are empty, comp plans are misaligned, and Q1 turns into a scramble. Steve explained that top-performing sales orgs begin planning in Q3. They audit team performance, open new job requisitions, and finalize comp structures long before the holidays.

“The mistake a lot of companies make is waiting too long,” Steve said. “They post a job, get 600 AI-optimized resumes, and then scramble to figure out who’s actually a fit.”

When leaders use the fall to assess gaps and clarify goals, they enter the new year with momentum. It’s not about moving fast for speed’s sake; it’s about making decisions early enough to give your team a strong foundation.

Evaluate Your Team Before You Hire

Hiring begins with clarity about who’s already on your team. Stack-ranking alone doesn’t tell the full story. Steve pushes leaders to dig deeper: is a rep underperforming because of skill gaps, lack of activity, or unclear direction?

He often asks his clients a question that flips the traditional power dynamic: What do you owe your sales team in order for them to succeed?

“Half the job of a sales manager is being a little bit of a psychologist,” he said. “The great ones know where people are at, set clear expectations, and help them focus on the right priorities.”

Before you hire externally, make sure you understand the internal realities. That clarity prevents you from over-hiring or misplacing talent.

Four Hiring Filters That Separate Top Performers

Once it’s time to expand your team, Steve recommends applying four consistent hiring filters:

• Behaviors: What daily actions does this candidate take to create pipeline and close business?

• Traits: Do they have the grit, curiosity, and resilience to thrive in your sales environment?

• Knowledge: How well do they understand your buyers, market, and product landscape?

• Culture Fit: Do they align with your team’s pace, values, and communication style?

Many companies treat hiring like guesswork, but top leaders treat it like a repeatable system. Steve explained, “I force my clients to get super clear about what makes their top people successful. Then we build consistent behavioral interview questions tied to those traits.”

This discipline removes bias and improves outcomes. You don’t need to chase polished resumes when you can identify proven behaviors that predict success.

Use Comp Plans as Leadership Tools

A comp plan is more than a payout sheet and deserves special attention to see if the plan is driving the desired behaviors and results. Does your comp plan truly mirror what the company values? If it rewards short-term revenue, expect short-term thinking. If it prioritizes renewals or upsells, your reps will naturally lean toward customer retention.

“The first thing I look at is the comp plan,” Steve said. “It tells me what the company actually wants. Are they rewarding revenue this year or setting me up for next year’s growth?”

Heading into 2026, take time to align compensation with your strategy. Decide whether your team’s mission is new acquisition, expansion, or balanced growth. Then design incentives that pull everyone in the same direction.

Balance Today’s Wins with Tomorrow’s Growth

Every sales leader knows the temptation to sandbag deals for the next quarter. Steve warns against it. “If you think you can delay deals now to make next year easier, you’re playing a dangerous game,” he said.

The smarter play is transparency. Bring data to the table (think: conversion rates, deal cycles, and pipeline health) so that next year’s targets reflect reality. Sales leaders who communicate early help finance and operations set achievable numbers, creating alignment across departments.

When to Leverage Fractional or Contract Talent

Not every problem needs a full-time hire. One of the biggest trends Steve sees is companies using fractional or contract help to test strategies. A fractional CRO might redesign a comp plan. A temporary BDR team could validate a new market without disrupting the daily flow of your current team.

This approach gives leaders access to high-level expertise without permanent overhead. As Steve joked, “When I was consulting, it shocked me how much people listened. When I was an employee, no one listened. Sometimes an outside voice makes all the difference.”

Fractional support can accelerate experimentation and help you find clarity before scaling.

Top-Grading for Growth

If you want to elevate your team’s performance, 2026 is the perfect opportunity to upgrade your talent bench. The concept of top-grading means replacing underperformers with higher-caliber talent to raise the overall average of your org.

Don't go around cutting people for "funsies" or sport. Really evaluate your roster and consider, What’s missing from this lineup if we’re going to crush next year’s targets? 

Maybe you need a senior closer, a strategic AE, or a sales operations expert. The goal is a balanced, intentional team that supports sustainable growth.

Build Culture and Consistency That Last

Hiring, comp, and planning only work if your culture supports them. Consistency in expectations and communication keeps teams aligned and confident.

“Everyone’s scared. Everyone’s tired,” Steve said. “The leader’s job is to make sure the team knows what success looks like and when they’re in trouble. If you don’t communicate that, they’ll fill in the blanks themselves — and it’s rarely positive.”

Great sales leaders replace confusion with clarity. They celebrate wins, address challenges openly, and protect trust like a core metric. Culture is the multiplier that turns strategy into results.

Action Steps for Sales Leaders Heading Into 2026

As we like to do in our articles, we throw a lot at you as a guide to keep after you listen to the episodes. Let's break this all down into simple chunks you can knock out this fall so you're going into Q1 ready to rip.

Heading into the new year, use this simple checklist from Steve’s playbook:

• Audit your team: Go beyond the leaderboard. Understand what’s driving success or holding reps back.

• Refine comp plans: Align incentives with the business outcomes your company truly needs.

• Clarify hiring filters: Define what success looks like before you start interviewing.

• Consider fractional talent: Bring in experts for specific challenges without adding long-term headcount.

• Reinforce culture: Keep communication clear and expectations consistent.

Each of these steps may seem small, but together they compound nicely. Leaders who plan early and communicate often enter Q1 with momentum while others are still catching up.

Final Takeaway

Sales leadership is both strategy and stewardship. It’s knowing the numbers while guiding the humans behind them. As Steve Levitt shared, “You can’t succeed alone without your team. Help them. Carry their concerns upward and bring clarity back down. That’s the job.”

Start now. Evaluate, plan, and lead with purpose. The teams that thrive in 2026 will be the ones whose leaders were already preparing today.

You can connect with Steve on LinkedIn here