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😎 Sean the tech sales hiring machine, breaking down a $1mm deal, and lying on your resume

Sean helped 100 people land their dream sales roles, let's say he knows a thing or two about getting people hired.

June 25, 2025

IN THIS EDITION

Can you believe we made it to double digit editions? There has to be a crazy stat out there about all of the newsletters/podcasts that never did.

Don’t worry we’re not going anywhere anytime soon.

Here’s what you can expect from edition #10 today:

  • He helped 100 people break into tech sales - Sean Alkis

  • Breaking down a million dollar deal

  • Should you lie on your resume?

  • And more…

Want to be featured in BOS? Know somebody that we should feature? Please submit your information here for consideration. You don’t have to be making one billion dollars per year so long as sales has enabled you to live a pretty cool life. Thanks!

LIVE FROM THE SALES FLOOR

Recent Events

  • Step-by-step: How this AE closed a $1,000,000 deal (Mike Gallardo)

  • Top 10 public tech companies ranked on sales rep outlook (Ryan Walsh)

  • Selfish plug: We passed 500 subscribers on Instagram! You should join us

Tips + Tricks

  • How to handle burnout when working less is not an option (@teodor_io)

  • Steal this sales productivity cheat sheet (Harris Halkis)

  • Why you shouldn’t ever compete on price lol (Will Schryver)

  • Handle the “you’re pretty expensive” objection (No_Libarian9791)

Other Stuff

OUR SPONSOR

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SELLER’S SECRETS

Who is Sean Alkis, and what is he up to?

Sean Alkis is an Austin-based former mid-market tech AE who now runs two tech sales-related businesses.

1) Tech Sales Trailblazers: A coaching business that helps people land their first or next tech sales role.

2) Tech Sales Talent Partners: A recruiting business helping companies find their dream sales talent.

Connect with Sean: Instagram, LinkedIn, TikTok, Youtube.

Check out Sean’s full interview on Youtube, Spotify, or Apple Podcasts.

Sean’s come-up story (in 9 bullet points)

  • Senior at college, discovers online business via Twitter.

  • Interned at Northwestern Mutual, learned foundational sales skills.

  • Got to experience high turnover and intense sales pressure early.

  • Transitioned into tech sales through connections made in Austin.

  • Hustled valet and bartending alongside tech sales to boost income.

  • Climbed the ranks from SDR to pres. club mid-market AE at Procore.

  • Joined a program to learn content, built his coaching on the back of it.

  • Founded Tech Sales Talent Partners, expanding into recruiting.

  • Recently quit the corporate gig to fully focus on his businesses.

Sean’s sales alpha and best practices

1. Optimize titles to capture recruiter interest

Sean emphasized the importance of matching your job titles to industry standards like "Sales Development Representative" or “Account Executive” to make sure your LinkedIn profile actually gets found by the people you want to find it.

Recruiters search using exact keywords, so simply adjusting your title to a commonly searched term will significantly increase visibility and opportunities from recruiters.

2. Maximize internal team networking to fast track promos

To fast-track promotions, Sean advises building relationships not just with direct teammates but also with managers and decision-makers in other departments.

Pre-interview networking transforms formal interviews into casual conversations, boosting your chances significantly.

When Sean went for his internal AE promo from being an SDR, the conversation with the manager was 10x more smooth because they had already connected on it weeks prior.

3. AI-enhanced efficiency in outbound recruiting or selling

Sean has figured out how to automate a fair amount of a high-paid sales reps work using AI and tools like Clay. Not only is he saving a ton of time, but money as well. He operates a fully scaled outbound system for a literal fraction of what a traditional SDR would cost him.

Keeping overhead low and output high has allowed his recruiting business to gain pretty significant traction in just month #1.

[Side note: If you want a deep run down on cool Clay uses for B2B prospecting, listen to podcast #3 with Kellen Casebeer, really good stuff]

How it feels to quit your corporate gig and go “all-in” on your own businesses

Traction: Implement these 4×4 tips from Sean and see if they help you out

#1: Secure your internal promo the easy way

  • Be sure to state your career goals to your manager early on.

  • Build relationships within your company early, social and learning benefits.

  • Consistently aim for top-quartile performance (focus on hustle stats if needed).

  • Objective: Have the promo convo before the promo convo.

#2: Optimize your LinkedIn to have work come to you

  • Have a professional headshot and a nice banner photo at minimum.

  • Rewrite job titles with the role you aim to secure, research industry if needed.

  • For experience: List out concise, results-oriented descriptions.

  • Proactively grow your LinkedIn connections to build further credibility.

#3: Sell the relevant experience, not your job description

  • Frame prior experiences around outcomes that matter.

  • You need to use industry-compatible language for the role you want.

  • Highlight quantifiable results like SQL’s and quota attainment.

  • Show you can adapt by focusing on sales capability rather than job specifics

#4: How to safely quit a high-paying corp. gig for your own business

  • Stretch the delta between earnings and spending as much as possible

  • Keep the car that gets the job done (Sean’s case: 2011 Honda Pilot)

  • Lifestyle upgrades can wait until they’re a no-brainer (Sean’s case: New Audi)

  • Rent is everyone’s biggest expense, live with others as long as you can

Check out Sean’s full interview on Youtube, Spotify, or Apple Podcasts.

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