How to Shift From Transactional to Strategic Brokerage

Nobody likes talking to salespeople. So don’t be one. Be a problem-solver. Be a pattern-breaker. Be the person they trust enough to bet their next promotion on. I didn’t go to school for sales. Pretty sure none of us did. I was on the pre-med track at UCLA. Studied psychology. Planned to become a psychiatrist. Somewhere between Freud and finance, I found something more interesting: Why people buy. Why they don’t. And why most GTM teams get it completely wrong. One thing stuck with me from that world: Diagnose before you prescribe. In medicine, you’d lose your license if you recommended treatment before understanding the patient. But in sales? Too many are still showing up with: “Here’s our demo. Want to talk pricing?” That’s not strategic. That’s malpractice. 🔁 FROM TRANSACTIONAL TO TRANSFORMATIONAL 🪧 1. LET’S RETIRE THE WORD “SALES” Controversial, maybe. Job titles shape behavior. If your reps think their job is to sell, they’ll pitch. If they think their job is to solve, they’ll listen. And if they believe their job is to transform, they’ll lead. ✅ Quick Win: Reframe your team’s mission. You’re not in sales. You’re in "Strategic Growth", "Problem Resolution", or "Business Impact Enablement" — whatever aligns with your buyer’s world. 💬 2. SEMANTICS MATTER If you say, “We just need to prove value, and then we can grow together,” they hear: “You’re not the priority — we’re already looking past you.” Buyers pick up on intent before you even get to the pitch. Words shape perception: • “Operational wins” instead of “value prop” • “Workflow gaps” instead of “pain points” • “Strategic priorities” instead of “objections” 🛠️ Quick Win: Pull your last 5 outbound messages. Replace every sales-y phrase with language pulled straight from their world — investor memos, recent press, and even job descriptions. 🧠 3. PSYCHOLOGY > PITCHING Sales isn’t about persuasion. It’s about alignment. Your buyer isn’t a persona. They’re a person — navigating pressure, risk, and scoreboard metrics. Great reps don’t pitch. They investigate. They ask better questions. They diagnose before they prescribe. I worked with a Director of Risk who wasn’t worried about price — she was worried about getting blamed if rollout failed. We reframed everything around internal wins she could take to leadership. That’s what earned the deal. 🔍 Quick Win: Before your next call, write down 3 motivators your stakeholder might have: Recognition, Control, Simplicity, Security, Legacy. Then tailor your questions accordingly. I’ve watched reps lose 7-figure deals because they showed up to pitch… …instead of showing up to understand. Don’t be that rep. Be the one who diagnoses with empathy, delivers with impact, earns belief that compounds — and gets invited back to build what’s next. Want my Diagnostic Question Bank Framework? Drop a “🧠” in the comments, and I’ll share it once live.

Sales teams that have transitioned from transactional to value selling have a counterintuitive approach to both disqualify and do deeper discovery at the same time (that actually works). Put simply, they work backwards from the prospect’s desired business outcomes through to the pain they’re currently feeling. It starts with getting to know what the person in front of them wants to achieve - do they have career goals, anxieties, aspirations that drive them? Is there an upcoming event that has a significant impact on any of those things? Zoom out to what their team and function wants to achieve and understand how that is measured and assessed. Work towards the inputs that are needed to achieve those goals/metrics. Finally - identify the blockers that are stopping them from getting there. This helps get early buy-in that you will need to get through those blockers together in order to reach their goals. Customers don’t always know exactly what solution they need and how to navigate the maze of challenges on the way there. But they do know what metrics they are assessed against, and they do know what’s expected of them in their role and their function (if they’re leading it). So start there. Make it really obvious that you understand their personal challenges, and work backwards to see if you are the right fit to help them get to that desired state. That way, you get an understanding of whether there’s real need and urgency for the deal, as well as what the desired state is, and what challenges need to be overcome. Sometimes to see clearer you just need to invert.

Agency says: "we keep getting blocked by our point of contact". We want access to leadership. They're the gatekeeper. What gives? We're supposed to be the experts right? How are we supposed to add value when we have no exposure or influence over the plan, the budget or the (other) vendors at play? That's what we all want to say :) In reality breaking through the gatekeeper requires a tid-bit of psychology... Steve Patti and I worked on a path to go from transactional to strategic. Step 1: Just perform Nobody is going to bat for you if you're not delivering what you promised. That said, how we're measured is typically WAY OFF from what your point of contact is being measured on. Three questions you should be asking yourself: 1. Do we know what key marketing initiatives our client contacts have been tasked to deliver? 2. We know what marketing/agency performance information our client contacts are required to present and in what format? 3. Do we know where (performance metrics) our client contacts have consistently under performed? If you can answer YES to all these you've probably got TRANSACTIONAL influence... you've got some say in the tactics you've been contracted for and how you allocate budget / time within those activities. Step 2: Relationship Your point of contact won't put themselves at risk... they'll block you until they feel you've got THEIR best interests in mind. Ask yourself: 1. Do we know what challenges our client contacts are struggling with most? 2. Do we know how our client contacts are being measured personally? 3. Do we know which internal stakeholders are the biggest blockers to the success of our client contacts? Answer yes and you'll have PERSONAL influence... now you can team up to expand your value in the organization and remove barriers. Step 3: Access to decision makers. Ask yourself: 1. Do we know what business outcomes are most important to the executive team? 2. Do we know what frustrations the executive team has with their Marketing team? 3. Do we know who (executives) our client contacts struggle to engage? We'd like to think we've got strategic relationships with our clients... but if you're answering NO to these questions i'd argue that you're stuck in the transactional vendor zone. Go ask your account managers these questions. Plan accordingly. How are your account managers measuring their client relationships? #agency #servicedesign