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- The Rep Report (June 2025)
The Rep Report (June 2025)
Curated by ClosedWon Talent. Straightforward, practical hiring advice from recruiters who help Sales & GTM pros land better roles and succeed.
Jay Green
June 25, 2025
📢 Welcome to The Rep Report!
You’re here because you want to make smarter moves, not just jump when things go sideways. In each issue, we’ll share practical advice, featured roles, and real-world guidance from recruiters who help Sales & GTM pros get hired every day. Let’s get into it.
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🌟 ClosedWon Updates
Updates from our team and new content to help you grow your Sales & GTM career.
We’ve launched a free resource hub packed with guides, templates, and tools for every stage of your job search. Check it out here.
Got a question or a topic you want us to cover? Just reply and we’ll respond back.
💡 The “Won” Thing You Should Know
One tactical tip each month to help you stand out and get hired…straight from the front lines.
Anchor your answers in their ICP…not just your past experience.
If you're switching industries or stepping into a new vertical, you need to prove you’ve thought through how to sell to a different kind of buyer. It’s not enough to say what you’ve done…you need to show how you’ll adapt.
This comes up in questions like:
“How would you approach selling our product?”
“This role’s different from your last one…how would you adjust?”
“Walk me through a discovery call with our buyer.”
If you’ve sold to IT, but this role targets finance leaders buying AI software, here’s how you stand out:
“Since your ICP is finance leaders at mid-sized companies, I’d shift my messaging to focus on accuracy, audit-readiness, and cost efficiency. Compared to IT buyers where I emphasized integration and scalability. Finance cares more about reporting workflows and risk mitigation. That would shape how I handle discovery, objections, and even my outreach strategy.”
That kind of answer shows:
You understand who they sell to
You’ve thought through the sales motion
You’re not just reusing the last playbook…you’re already adapting to this one
Bottom line: When you speak in the buyer’s language (even before you're hired) you go from “qualified” to “ready.”
🔥 Featured Job Openings
Each month, we highlight a few roles we’re actively hiring for like AE, SDR, CSM, and more. If one looks like a fit for you (or someone you trust), let us know. We offer referral bonuses for successful placements.
Interested in one of these roles? Or have a friend to refer? Go here!
🎉 What Got Me Hired
Real stories from sales & GTM pros who landed great roles and how they did it.
Have a success story to share? Hit reply to drop your knowledge!
📢 Rep Shoutouts
Each month, we’re highlighting sales & GTM pros who are doing the work, paying it forward, or just supporting the mission.
Andre McLaughlin: Just hit 9 years at Amazon & has worked at only 3 companies in 16 years. Legendary!
Gui Groscos: Thanks for all the support on our posts & congrats on your new role!
Maranda Dziekonski: Congrats on joining Fexa as Chief Customer Officer!
Rico DePaolis: Landed a great role after being laid off. Congrats!
Ben Bowles: Successfully landed an awesome role at Freshworks as Lead - Revenue Enablement!
Lindsey Parsons: After 6+ years at Kindful/Bloomerang, she made the move to Feathr as Associate Director of Sales!
Dave Murphy: Just joined Tami as the head of GTM. Way to go!
🙋Ask ClosedWon
Real questions from real reps…answered by the team at ClosedWon Talent.
Question
I’ve had a rocky few years with my last 3 roles all lasting about a year. I’ve built up some valuable skills and experience in my industry but am wondering if I should change paths by leaving SaaS and moving into consulting. What’s your advice?
Answer:
A career pivot is a big move…and you don’t want to make it just because you’ve had a rough stretch.
Start by getting brutally honest about what’s driving the urge to switch. Are you burned out on SaaS? Tired of startup chaos? Chasing stability? Whatever it is, write it down. Then make two lists: one for what your current track still offers, and one for what consulting could give you. Be specific i.e. skills you’ll use, income potential, control over your time, etc.
Finally, pressure-test your motivations. If it’s about flexibility or stability, would a better-run SaaS org solve that? If it’s about feeling stagnant, are you running from the industry or from your current experience in it?
If consulting aligns better with what matters to you and you're not just reacting to recent pain, then move forward with intent!
Have a question you want answered? Ask away here.
📖Guides and Resources
Startup Stage Breakdown: From seed to public, each stage of a company comes with trade-offs. This guide breaks down what each one actually feels like so you can target the right environment.
Not All Startups Are Equal: Early-stage doesn’t always been scrappy. This guide breaks down the different types of startups so you can avoid chaotic environments and find one that fits your speed.
Watch our latest Instagram videos for some tactical tips, interview prep, hiring insights, and more. 👇
🖋️ Stay in Touch
That’s it for this edition of The Rep Report. Feel free to reply with any questions or feedback. Thanks and see you next month!