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Wednesday Jan 28, 2026

Software Sales Career Guide: Pay, Progression & How to Break In

Wednesday Jan 28, 2026

Today we sit down with John Lack, Global Head of Sales Development at Airtable, to demystify the world of software sales as a profession. John breaks down the immense rewards of the industry—from earning six figures right out of college as a successful BDR to mastering the "autonomy, mastery, and purpose" of high-level tech sales.

We explore why the BDR role is the most critical time in a career for building foundational grit and why 90% of AE struggles stem from poor front-end pipeline generation. John also shares his own unconventional journey, starting as a BDR at age 30 and scaling teams through massive growth phases at Oracle and MongoDB.

🙌 Thanks To Our Sponsor! Aurasell AI: https://www.aurasell.ai

🏹 Key Topics Covered

00:00 - Intro

01:53 - Software Sales as a High-Trajectory Profession

03:48 - The Six-Figure Entry: SDR/BDR Realities

06:47 - Why PG Sets You Free

10:27 - Grit and Resilience: Pushing the Boulder

16:51 - How to Assess the Right Organization 20:25 - Uncommon Investment in Development

33:28 - John’s Story: Starting as a BDR at 30

43:32 - The AE and BDR Partnership Dynamics

💥 3 Biggest Lessons:

Pipeline Generation is the Foundation of Success: Most Account Executives who struggle do so because they lack consistent pipeline generation skills from the front half of the sales process. The BDR role is not just a stepping stone; it is where you learn the "meat and potatoes" of sales—doing the gritty work in the dark, from cold calls to disqualification, that eventually sets a field seller apart.

Seek "Uncommon Investment" in Development: When interviewing, candidates must challenge organizations on their training programs. A high-quality program can clearly articulate its methodology (Learn, Practice, Do), validates skills through real-world application, and provides double the industry standard of coaching time—dedicating specific hours to both pipeline strategy and individual skill development.

Habits Determine Your Fate: Success in sales is fueled by a consistent "operating rhythm" and discipline. Resilience—the ability to view 70,000+ cold calls as a way to learn rather than just experiencing rejection—and the discipline to maintain consistent prospecting habits are what ultimately determine a leader's career trajectory.

💬 Notable Quotes

"You can easily make six figures right out of college as a successful BDR and it just goes up from there".

"PG is life. It sets you free".

"You don't determine your fate. You determine your habits and your habits ultimately play a huge part in determining your fate".

"I made somewhere in the neighborhood of 70,000 plus cold calls in my life... that teaches you a certain level of resilience".

"There is no AI without APIs... AI is not going to have that first conversation and really do phenomenal qualification".

🙌 Thanks for listening!

This episode was hosted by Simon Kouttis and Ollie Kuehne, founders of Hunters & Unicorns, and post-produced by the team at videoforce.pro. If you enjoyed this episode, please drop a like/share and subscribe to our channel!

🦄 Connect with Hunters & Unicorns

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Wednesday Jan 21, 2026

Finding Your Voice and Leading with Resilience, with Joe Eskenazi

Wednesday Jan 21, 2026

In this episode, we welcome Joe Eskenazi, CRO at Kong, to discuss the critical transition from an elite salesperson to a top-tier business leader. Joe shares how he bypassed the typical "salesperson" label by treating every interaction as a business consultancy, fueled by a concurrent MBA and an early career in sports broadcasting.

We dive deep into the reality of the CRO role—orchestrating cross-functional ecosystems rather than just closing deals—and the personal journey of managing high-intensity burnout. Joe also offers powerful advice on finding an authentic leadership voice and why organizations must prioritize leadership training to protect their talent.

🙌 Thanks To Our Sponsor! Aurasell AI: https://www.aurasell.ai

🏹 Key Topics Covered

00:00 - Intro

01:57 - The Reputation and Rise of a CRO

03:39 - Viewing Sales as Business Optimization

06:47 - The Calling Card for Success

13:50 - The Cross-Functional Ecosystem

19:30 - The Strength and Weakness of Intensity

25:00 - Navigating Burnout

33:14 - The Kobe Bryant Lesson

42:34 - Finding Your Own Voice

46:36 - The Era of AI Governance and APIs

💥 3 Biggest Lessons:

Be a Business Leader, Not a Sales Leader: To reach the executive level, you must shift your mindset from selling products to solving strategic business challenges. Joe argues that a true business leader drives cross-functional alignment and won't do "bad deals" just for a commission because they are focused on the long-term health of the organization.

You Can’t Outwork the Job: High-performers often fall into the trap of trying to out-hustle every problem, which inevitably leads to burnout. True leadership requires ruthless prioritization, mental resilience practices like breathwork or cold plunging, and recognizing that your effectiveness is compromised if you neglect your health or family.

Never Compromise the Standard: Influenced by mentors like Cedric Pech and Luca Lazzaron, Joe believes in maintaining an unshakeable standard of excellence. He uses the "Touch the Line" philosophy to remind leaders that shortcutting small details eventually leads to personal and professional erosion.

💬 Notable Quotes "Find your voice. Find out who you are as a leader". "I tell AEs who become leaders, you can't outwork the job. Just know that". "I realized that I love what I'm doing because I love to help businesses optimize and transform". "Preparation was always my calling card... I absolutely have a big fear of failure". "There’s no AI without APIs... we like to be the picks and shovels leading to the gold".

🙌 Thanks for listening! This episode was hosted by Simon Kouttis and Ollie Kuehne, founders of Hunters & Unicorns, and post-produced by the team at videoforce.pro.

If you enjoyed this episode, please drop a like/share and subscribe to our channel!

🦄 Connect with Hunters & Unicorns

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Wednesday Jan 14, 2026

Stop Being Nice, Start Being Kind: The Cultural Shift That Built Kong

Wednesday Jan 14, 2026

In this episode, we sit down with Carl Mattsson, VP & GM EMEA at Kong, to discuss one of the most remarkable scaling journeys in the industry. Carl joined Kong when it was at just $1M ARR in the EMEA market and has since spearheaded its growth to nearly $100M ARR. We explore the unique sales principles that shaped the organization, the "heart surrounded by science" culture, and how Carl navigated the transition from a single-product company to a dominant AI-governance platform. Carl also shares the incredible story of a founder’s personal commitment that kept him at the company during a critical turning point.

🙌 Thanks To Our Sponsor! Aurasell AI: https://www.aurasell.ai

🏹 Key Topics Covered

00:00 - intro

02:30 - Joining Kong at $1M ARR

04:34 - Pivoting from Family to Team Culture

07:42 - Hiring for Character over Industry Experience

17:22 - The Open Source to Enterprise Transition

22:31 - The Pasta Story: A Founder's Commitment

31:46 - Kong’s Role as the AI Governance Layer

50:39 - Scaling Careers in 4-Year Increments

💥 3 Biggest Lessons:

Hire Character, Teach Technology: In the early stages of a high-growth startup, it is more effective to hire for sales character and drive than for specific industry knowledge. Carl emphasizes that while API technology can be taught, the innate curiosity and grit required to traverse from developers to the C-suite cannot be coached. Heart Surrounded by Science: While many elite sales organizations focus 99% on "science" (metrics and process), Carl advocates for a culture of kindness over niceness. This means having the "heart" to challenge each other uncomfortably and care for the human, while using "science" to provide the repeatable structure needed for scale. The "Because Of" Journey: Carl encourages leaders and reps to seek out roles where their personal contribution leaves a visible mark on the company's trajectory. Success in a "because of you" environment sharpens a salesperson more than a fully-oiled machine, preparing them for the highest levels of business leadership.

💬 Notable Quotes

"Our culture should be: we’re not going to be nice every day, but we’re going to be kind".

"I can teach it (the playbook), but I can't teach you character".

"If you're in something you believe in... I don't tend to pick up the phone, even when great people like you call in". "We put the customers first, the company second, and ourselves last".

"I look at my career in four-year increments... that’s always helped me be pretty focused about where I need to go and learn".

🙌 Thanks for listening!

This episode was hosted by Simon Kouttis and Oli Kuehne, founders of Hunters & Unicorns, and post-produced by the team at videoforce.pro. If you enjoyed this episode, please drop a like/share and subscribe to our channel! 🦄 Connect with Hunters & Unicorns Website: http://huntersandunicorns.com Twitter: / huntersun1corns Instagram: / huntersandunicorns Blog: http://huntersandunicorns.com/blog #softwaresales #huntersandunicorns #playbookuniverse

Wednesday Jan 07, 2026

Beyond the Sales Book: The Emotional Secret to 10X Career Growth

Wednesday Jan 07, 2026

In this episode, we welcome Steve Rog, CRO at Cyera, one of the fastest-growing technology companies in the world.

Steve opens up about his journey from a technical networking background to becoming a high-impact leader in cybersecurity. We unpick how he landed one of the industry's most sought-after CRO roles and why Cyera’s culture of humility and teamwork keeps them winning.

Steve shares profound lessons on seeking out mentors, the critical importance of Emotional Intelligence (EQ) in delivery, and why he views leadership as a responsibility to help others reach their "ceiling".

🙌 Thanks To Our Sponsor! Aurasell AI: https://www.aurasell.ai

🏹 Key Topics Covered 00:00 - In this episode

01:53 - Landing the Industry's Hottest Role

02:45 - Culture: No One is Bigger Than the Team

05:02 - The Science Behind the Playbook

06:45 - The Debt of Gratitude: Seek Mentors

13:05 - Overcoming Early Career Insecurity

35:57 - EQ: Why the Way You Deliver Matters

39:15 - A Turning Point: When My Boss Joined Me

💥 3 Biggest Lessons:

EQ is About Delivery, Not Softness: Emotional Intelligence isn't just about being "likable"; it's about the strategic delivery of information. Steve emphasizes that the way a leader delivers good or bad news determines how it is received and acted upon, requiring the leader to put themselves in the other person's shoes.

Authentic Leadership is Altruistic: The most authentic form of leadership is surrounding yourself with people better than you and not being insecure about having "weapons" on your team. Steve attributes his success to Cyera's altruistic culture, where teams prioritize the customer first, the company second, and themselves last.

Active Mentorship Drives Careers: You cannot wait for an introduction; you must proactively seek out mentors and ask for help. Steve advocates for paying this forward by investing in everyone from BDRs upward, ensuring team members have the guidance they need to navigate "highs and lows" without entering a tailspin.

💬 Notable Quotes

"I love seeing the team win. I love seeing career progression and I love the thought that I'm helping people achieve their career goals".

"No one person is bigger than the team".

"Measure six times, cut once. It's the philosophy across the company".

"You almost have to have imposter syndrome to go figure it out". "You can't coach charisma, you can't coach likability... and you can't really coach desire".

🙌 Thanks for listening! This episode was hosted by Simon Kouttis and Oli Kuehne, founders of Hunters & Unicorns, and post-produced by the team at videoforce.pro.

If you enjoyed this episode, please drop a like/share and subscribe to our channel!

🦄 Connect with Hunters & Unicorns Website: http://huntersandunicorns.com Twitter: http://twitter.com/HuntersUn1corns Instagram: http://instagram.com/huntersandunicorns Blog: http://huntersandunicorns.com/blog

SEO Tags: Steve Rog, Cyera, CRO, Sales Leadership, Cybersecurity, Servant Leadership, Emotional Intelligence, Mentorship, GTM Strategy, Force Management, Career Progression, Software Sales, Hunters & Unicorns

Tags: #softwaresales #huntersandunicorns #playbookuniverse

Friday Nov 28, 2025

Will AI Replace Sellers or Make Them Unstoppable?

Friday Nov 28, 2025

Jason Eubanks is back to answer the question every revenue leader is asking: Will AI kill sales jobs or make great sellers unstoppable?

He drops hard stats (91% of B2B teams missed quota, top 25 % drive 80% of revenue at 11× productivity) and explains why AI is a superpower for elite performers, a wake-up call for the bottom quartile, and a complete game-changer for SDR outreach, buyer trust, and hiring. If you lead a sales org, this 35-minute conversation is required listening. 🙌

Thanks to Our Sponsor! Aurasell AI

The first AI-native GTM platform: https://aurasell.ai

🏹 Key Topics Covered

00:00 - Intro & Jason returns

01:38 - AI: replace or superpower?

03:07 - Top 25% dominate revenue

04:38 - 91% teams miss quota

09:40 - AI’s impact on SDRs

12:46 - Outreach volume vs buyer fatigue

16:52 - Human trust + real-time signals

25:14 - Hiring for the AI era

28:25 - Will AI make sellers lazy?

31:12 - Keeping top talent engaged

💥 3 Biggest Lessons:

1. AI Widens the Performance Gap Top 25 % already produce 11× more — AI will make them unstoppable while exposing under-performers.

2. Bottom Quartile Must Adapt Fast If you don’t aggressively adopt AI tools, you’ll fall further behind as others 2–4× their productivity.

3. Hire Character, Teach Skills Work ethic and engagement can’t be automated — get these right and AI turns good sellers into great ones.

💬 Notable Quotes “AI will be a superpower… it will unlock new levels of productivity that allow your top sellers to become even more productive.” “91 % of all B2B sales teams didn’t hit their revenue targets.” “80 % of the revenue was generated by only 25 % of the sellers.” “I don’t buy that AI makes sellers lazy — laziness exists for other reasons.”

🦄 Connect with Hunters & Unicorns

X: http://x.com/HuntersUn1corns

#softwaresales #huntersandunicorns #playbookuniverse

Wednesday Nov 26, 2025

Meet our NEW Sponsor!

Wednesday Nov 26, 2025

In this episode, we talk to Jason Eubanks, CEO and Co-founder of Aurasell (our brand NEW Sponsor!), about his transition from a 20-year go-to-market operator to a builder and founder.

Jason shares the exact moment he became obsessed with solving a major product problem, the complexity and low productivity caused by massive tool sprawl (over 20 products) and unintentional data silos in the go-to-market stack. He details the crucial steps of founding Aurasell: partnering with a complementary CTO, validating the huge market problem (estimating over $1 billion in services spend), and securing a significant seed round to build the world's first AI-native CRM platform focused on customer-problem-centric design.

🙌 Thanks To Our Sponsor!

Aurasell AI: https://www.aurasell.ai

🏹 Key Topics Covered

01:36 - Founder Journey & Co-Founders

03:24 - From Operator to 3:15 a.m. Spark

05:00 - VC Detour & Market Gap

07:42 - Tool Sprawl & Unified AI Context

11:22 - Mapping the Problem to $30M Seed

💥 3 Biggest Lessons:

The Spark of Product Obsession: Jason’s 20-year career as a CRO never led him to chase founding a company—until he woke up obsessing over a core product problem firsthand: the low productivity and operational cost caused by 20+ disconnected tools in the go-to-market stack.

Tool Sprawl Handicaps AI: The reliance on 20+ legacy SaaS products unintentionally creates data silos where crucial contextual metadata lives, rather than the core CRM. When companies try to "sprinkle" AI on this brittle structure, they severely handicap the potential for high-quality automation.

The Opportunity is in AI Native: To maximize productivity and solve the tool sprawl problem, the necessary solution is a single, AI-native platform built with a unified logic layer. This approach moves beyond small "AI tricks" to actionable automation that frees expensive sellers to attack the market.

💬 Notable Quotes

"I don't wake up at 3 in the morning and obsess over product. And then one day I did wake up at 3:15 in the morning obsessing over a product problem."

"I think it's important to make sure that your co-founding partners are complementary in skill set, like Minded and Alind on the problem."

"On average, every dollar of software you spend, historically has carried with it $3 of services." "The problem... is that those sellers are being asked to interface with... the contextual awareness that allows us to use AI to automate with high quality outcomes, often that contextual awareness lives in the metadata."

🙌 Thanks for listening!

🦄 Connect with Hunters & Unicorns

Twitter: / huntersun1corns

Instagram: / huntersandunicorns

SEO Tags: Jason Eubanks, Aurasell, AI Native CRM, Founder Journey, CRO to CEO, Tool Sprawl, Data Silos, Sales Productivity, GTM Platform, Seed Round, Co-founder, Venture Partner #softwaresales #huntersandunicorns #playbookuniverse

Wednesday Nov 19, 2025

Beyond the Sales Playbook: The #1 Skill for Getting Ahead in Tech with Emma Maslen

Wednesday Nov 19, 2025

In this episode of the Great Leaders UK series, we welcome Emma Maslen, author, angel investor, and founder of inspir'em.

Emma draws on her successful career in large organizations like SAP and BMC to discuss the crucial difference between theoretical playbooks and their real-world, behavioral application. She stresses that the playbook is a framework to drive curiosity and risk mitigation, not a tick-box exercise. Emma also shares why networking is a constant professional necessity, detailing the common mistakes people make and how leaders can intentionally build their networks to gain knowledge and accelerate their careers.

🙌 Thanks to Our Sponsors! PGAI: https://www.getpg.ai Selr: https://selr.ai

🏹 Key Topics Covered

01:40 - What's inspir'em?

03:06 - It's about curiosity, not checklists

04:36 - The flaw of the "100% Med-Pic score"

06:50 - Why the playbook can't be a preach

11:09 - Leaders not present during sales training

12:05 - Verbalizing questions and intentionally

14:13 - Customizing the discovery process

16:48 - Discovery is a Two-Way Dating Process

18:05 - Career Shift from corporate MD

25:37 - The Power of Networking

30:50 - Good vs. Bad Networking

35:51 - Networking for internal success.

41:05 - The value of community

51:37 - The value of coaching

💥 3 Biggest Lessons:

The Playbook is a Framework for Curiosity, Not a Checklist: When Meddic, Med-PICC, or any framework becomes a mere tick-box exercise, it becomes pointless. It should instead function as a tool to continuously drive curiosity, expose risks in your pipeline, and prompt deeper questions.

Winning Requires Leadership Buy-In (Not Dictation): Sales training fails when executives and leaders see it as something "done to the sales team," often not even attending the training themselves. Successful adoption requires the playbook to be a dialogue driven by empathy and shared accountability.

Networking is a Professional Must (Not Just a Job Hunt): Many people only realize they have a networking problem when they desperately need a new job or advice. Good networking is about proactive investment: focusing on who you can help, giving back to the network, and making small, specific asks to gain knowledge, not just taking.

💬 Notable Quotes "There are still a lot of organizations out there that think Meddpicc is something to be done to the sales team." "If it's become a tick box exercise, you might as well just get rid of it because it becomes pointless." "It should be a framework to drive curiosity." "People feel like networking is about finding another job rather than being better at your current job." "I once said to him, why are you mentoring me because I'm like here and you're here and he said, because you've got a whole different perspective."

🦄 Connect with Hunters & Unicorns

Twitter:

/ huntersun1corns

Instagram:

/ huntersandunicorns

#softwaresales #huntersandunicorns #playbookuniverse

Wednesday Nov 12, 2025

Pre-Sales Masterclass: Earning Your Seat at the Elite Leadership Table with Julia Weimer

Wednesday Nov 12, 2025

In this episode of Great Leaders UK, we are joined by Julia Weimer, Director of Solution Engineering UKI at Wiz, to discuss the critical, often underutilized role of pre-sales in driving elite sales execution.

Julia shares her unique journey from Security Analyst in a SOC to leading a high-performing SE team , emphasizing why Sales Engineers must be viewed as equal business partners to Account Executives, not just technical support. She walks us through the importance of symbiotic relationships , leveraging structure like MEDDIC , and the power of empowering SEs to build technical champions.

🙌 Thanks to Our Sponsors!

PG AI: https://www.getpg.ai

Selr: https://selr.ai

🏹 Key Topics Covered

02:40 - SE/AE Relationships that Lead to Failure

05:27 - The Ideal SE Profile

07:40 - SEs as Deal Realists

11:50 - Driving Cross-Functional Alignment

16:15 - Nurturing Talent: Teaching Sales Methodology

23:45 - From SOC to SE: The Biggest Career Risk

27:57 - Diversity in Tech

39:17 - Recruiting Priorities

41:23 - The Motherhood/Career Balance

42:18 - Hiring for Entrepreneurial Mindset in SEs

🦄 Connect with Hunters & Unicorns

💥 3 Biggest Lessons:

The SE Superpower is Reality: The sales engineer's superpower is the ability to look into the reality of an opportunity and be a realist about its progression. This means SEs must be empowered to act as the credible technical person and trusted advisor in the room.

Structure the Sales Instincts: For many technically inclined SEs, the sales aspect is not natural. Leaders must provide structure (like teaching MEDDIC) and enablement to help SEs embrace sales methodology as a new skill set.

Symbiosis Drives Success: Amazing things happen when sales and pre-sales embrace a symbiotic relationship and work together. This partnership ensures accountability where neither the AE nor the SE is left with an uneven workload, helping to avoid deals from falling "out of whack".

💬 Notable Quotes "Sales engineering should always be treated as an equal partner to sales." "It was probably the biggest career risk that I've ever taken." "The balance is what I seek, and if you can find people that are really great with their people's skills and relatable... and also really like to solve problems. It's a perfect blend of both." "If you give us that type of platform and that type of respect in an opportunity, then the world is our oyster." "I really find that the sales engineering role is this gem of a role for those of us who are a little bit introverted, we really like tech and our skill sets are with the tech."

#softwaresales #huntersandunicorns #playbookuniverse

Wednesday Oct 29, 2025

How to Launch an AI Security Startup, with Kristian Kamber

Wednesday Oct 29, 2025

In this episode of the Playbook Universe, we speak with Kristian Kamber, CEO and co-founder of SPLX AI, about his journey from elite sales roles at AppDynamics and ZScaler to launching his own AI security startup. Kristian shares the inner drive and lessons learned, from a family restaurant business to the high-stakes world of Silicon Valley playbooks, that prepared him to lead a fast-moving, deeply technical company. He reveals the critical steps in finding the right technical co-founder, securing investment, and achieving product-market fit by listening intently to customers. This is essential listening for any sales professional considering the leap into entrepreneurship.

🙌 Thanks to Our Sponsors!

PG AI: https://www.getpg.ai

Selr: https://selr.ai

🏹 Key Topics Covered

00:00 - Intro

02:17 - The Inner Motivation to Be a Founder

03:44 - The Hard Decision: Leaving a Sales Career

04:47 - The Co-Founder Hunt and Validation

06:07 - Using Sales Skills to Vet an Idea

08:55 - The Turning Point: Securing Initial Investment

11:46 - The CEO Upskilling Curve: Investor Relations

15:28 - Sales Mindset as a Competitive Advantage

17:01 - Product Pivot: Listening to the Customer

20:19 - SPLX AI's Funding and Growth Timeline

24:30 - Evolving the CEO Role: From Sales to Strategy

27:38 - Hiring A-Players for an Early-Stage Startup

30:00 - The Unconventional Sales Mindset in the US

38:05 - The Importance of Moving Fast in Your Career

40:40 - Building Champions Outside Your Geo

47:49 - The 90-Day Product Innovation Cycle

50:46 - Advice for Aspiring Founders

💥 3 Biggest Lessons:

The Best Founder is the Best Salesperson: A founder must be the best salesperson in the company, constantly selling to customers, investors, partners, and potential hires. Sales experience provides a crucial competitive advantage in validating the product, building trust, and driving aggressive motion.

Finding a Co-Founder is Non-Negotiable: A sales-focused founder must pair with a deeply technical co-founder to balance skills and gain investor confidence. Kristian used his sales network and deep discovery skills to rigorously vet his co-founder's technical genius and commitment to the idea.

Master the Market, Not Just the Playbook: While sales playbooks are essential, true success in a fast-moving market like AI security requires listening to customers and being willing to pivot immediately. Kristian's team shifted their product focus after realizing the European market wasn't ready, proving that market adoption dictates the product roadmap.

💬 Notable Quotes "I'm super coachable when it comes to things I don't know, but I'm super strict about things I'm 100% I know how to do it." "I knew I need to find the right co-founder who knows how to build a tech so I can do with him the business because I know what I can't do." "You should thank God you made your co-founder. That was the turning point for me. I said, wow." "I knew I need to sell before I even have a product." "The biggest job of an early stage founder is getting term sheets. It's the biggest job."

🙌 Thanks for listening! This episode was hosted by Simon Koutis and Ollie Kuehne, founders of Hunters & Unicorns, and post-produced by the team at videoforce.pro. If you enjoyed this episode, please drop a like/share and subscribe to our channel!

🦄 Connect with Hunters & Unicorns