Coaching

Before You Hire Your First Sales Rep, Read This First

Most founders don't hire the wrong salesperson. They hire at the wrong time or into the wrong environment. Most hiring mistakes don't happen during the interview. They happen weeks before anyone ever posts the job. When founders come to us completely exhausted from running demos, managing operations, and updating the CRM at 10 PM, their first instinct is always the same: "I need to hire a salesperson to take this off my plate." I see this over and over. A founder hires an AE because they're burnt out. Ninety days and $25,000 later, they tell me, "The rep just wasn't very good." Maybe. But most of the time, we find out the setup wasn't ready in the first place. It wasn't the rep, it was the environment. Before you write a job post or run another interview, grab a pen. Seriously. Don't just read this. Let's find out where your setup actually stands.

Founder-Led GTM: Building Systems that Learn

Join GSD Coach & Designli on August 11th at 11:00 AM PST for a live workshop on scaling beyond founder-led sales. Discover practical frameworks to diagnose GTM bottlenecks, leverage AI to streamline your sales workflows, and identify the exact signals that tell you it’s time to make your first sales hire.

Why Your First Sales Hire Failed (And How to Fix It Before You Try Again)

"In the last six months I hired two people that didn't work out. It cost me time and money. Now I'm still the only one selling, and I need a salesperson in here yesterday so I can get back to working on the business." I was on the phone with an early-stage SaaS founder when he said that. I hear a variation of that sentence almost every week. When you're drowning in sales demos, customer support, and product updates, it's easy to view a sales hire as a quick escape hatch. You hire someone fast just to get relief. Then, ninety days later, you fire them. You're right back where you started, except now you're six months behind and out tens of thousands of dollars. Hiring a salesperson doesn't automatically buy back your time. If you drop a sales rep into a broken setup, it does the exact opposite: it doubles your workload because now you're managing someone who can't execute. Over the years, I've watched founders make the exact same three mistakes every single time they try to replace themselves in sales.

You Never Told Me This Could Happen

A Performance Improvement Plan (PIP) should never be a shock to your sales rep. If it is, the failure isn’t theirs—it’s yours as a leader. This guide breaks down why leaders avoid uncomfortable performance talks, the hidden cost of delaying them, and a simple, 3-part framework to ensure your reps always know exactly where they stand before a formal PIP is ever drafted.

Why Most Hiring Processes Fail: They Leave No Audit Trail

Most hiring decisions are made on gut feel. The problem is that gut feel leaves no evidence behind. When a hire succeeds, you cannot replicate it. When a hire fails, you cannot explain it. In this article, Travis Janko shares the simple hiring audit trail framework that helps SaaS founders replace opinions with evidence and build a repeatable hiring system.

Beyond Authority: Redefining TransActive Leadership in the 21st Century

We are witnessing a profound shift in what defines successful organizational leadership. The old top-down, "command and control" models are failing to keep up with the demands of the 21st-century economy. Today’s landscape requires more than just organizational authority; it demands a system built on unique value, trust, and influence. We recently distilled the key insights from a PMI.org webinar titled "Redefining Purpose & Leadership for the 21st Century." The session perfectly encapsulated the movement we support at GSD Coach & Recruiting: shifting from transactional management to powerful, networked leadership. Here is the blueprint for the modern leader.

Failing Upward — The Founder’s Guide to Aggressive Growth

Execution is the only cure for the two silent killers of startup growth: Perfectionism and Imposter Syndrome. This article explores the "Try Trap"—the hesitation that masquerades as intention—and offers a practical framework for building a culture of "Imperfect Action." Discover why shipping V1 and embracing the "awkward middle" of scaling is the only way to turn scars into an architected version of a better company.

The E.G.O. Test™: How to Spot a C-Player in 15 Minutes

Stop being "Glengarry-ed" by professional actors. Use this surgical 3-part framework to audit sales candidates for ownership, math, and self-awareness.

The Power of Ownership: Understanding Responsibility vs. Accountability in Leadership

As leaders, we often use the terms "responsibility" and "accountability" interchangeably. While closely connected, they represent distinct concepts that are crucial for building high-performing teams and a thriving organizational culture. Understanding this difference is the first step towards true empowerment.

The 2 Interview Questions That Reveal Everything

The Enduring Power of the Leader Who Has No Title: A 15-Year Reflection

The Enduring Power of the Leader Who Has No Title: A 15-Year Reflection. On July 9, 2010, I finished reading Robin Sharma's insightful book, The Leader Who Had No Title.

Lead with Clarity: The Secret to Unlocking Team Performance

Confusion is the enemy of execution.

Mastering Your "Non-Strengths": A Roadmap to Success

We often hear the advice to "focus on your strengths," and while that's undeniably important, it doesn't mean we can simply ignore our "non-strengths" – those areas where we're less naturally gifted or skilled. In fact, ...

Mastering Pressure: 4 Core Lessons from Coach K's Playbook

From the book "Beyond Basketball: Coach K's Keywords for Success" by Mike Krzyzewski, some super learnings on PRESSURE!

Beyond Deliverables: Your Team Growth Question

I’ve been thinking a lot lately about the rhythm of leadership and the conversations we have with our teams. Specifically, what’s the one question every leader should ask their team at the end of the week to genuinely un...

Your Team is a Garden: Cultivating Growth and Harvesting Success

Building a truly cohesive and high-performing team isn't just about assigning tasks and setting deadlines. It's a lot like gardening – a process that requires consistent care, attention, and the right environment to thri...

Sales Director: Own the First 90 Days

So, you’re the new Sales Director. Or maybe you’re the founder who just hired one. Listen up.

Uncoachable Reps: Spot Sooner, Act Faster

As a sales leader, your most valuable lever for building a high-performing SaaS sales team is coaching.

The Sales Director Quota Trap

If your Sales Director carries a full quota, you don’t have a coach.

The Human Side of Change: Why Your Response is Make-or-Break

Noticing how change is affecting others and how you deal with it will make or break your change initiative, which underscores a fundamental truth often overlooked: change is a profoundly human experience, and its success...

Stop Sabotaging Your Sales Team: 16 Coaching Mistakes to Avoid

I’ve seen it time and time again.

Navigating Change: Understanding the Human Element

I love this visual as a way to remember to recognize and acknowledge the various phases of change, especially critical if you are a change & transition management leader or even if you are experiencing change as a manage...

The Power of One

by Ashish Ram

Should You Fire That Sales Rep? A Gut Check for Founders

If you're a B2B SaaS founder, you’ve either faced this dilemma—or you will.

Your Voice, Your Presence: Communication That Matters.

Several years ago, I had the privilege of learning some invaluable lessons about effective communication from Lindsey Cohen, our Communications Director at Visible. These lessons have had a lasting impact on me, and I be...

What High-Performing SaaS Sales Teams Actually Do Differently

What sets the best SaaS sales teams apart? It's a combination of these key elements, executed consistently.

Common sales coaching mistakes to avoid

Title: Unlocking Potential: The Top 15 Sales Coaching Mistakes That Crush Teams

Rooted & Radiant: Effectively Managing Up

Learning to "manage up" is a lot like being a flower in bloom. I have learned you have to have an outward, honest, and polished perspective as well as have strong boundaries and "roots" hidden below the ground and within...

Unlock Your Team: The 5 Roles of High-Performing Sales Coaches

Are your sales coaching sessions falling flat? Leading a sales team is one thing.

The Transparency Filter: 2 Hacks to Stop Wasting Time on Interviews

How many hours have you wasted in first-round interviews with candidates who were never going to be a fit? We’ve all been there. Ten minutes into the call, you realize there’s a massive disconnect on salary, expectations, or the actual nature of the work. Now you’re stuck in a "polite" 30-minute conversation while your real work sits untouched. It’s a drain on your energy. It’s a drain on your team. And it’s completely avoidable. The solution isn't "better" interview questions—it’s a more transparent process. At GSD, we use two simple hacks with every search. They act as an automated filter: they push the "Passengers" away and pull the "A-Players" in.