StartUp Hiring

Simon McSorley. Founder of StartUp Hiring and Crew Talent Advisory.

StartUp Hiring is a podcast about what really happens when startups grow, through the people they bring in. Each episode features someone who’s lived it: founders making early hires, operators landing roles, and people building careers inside startups. We dig into what worked, what didn’t, and what they’d do differently. If you're building a team or trying to join one, this is for you. Subscribe to the StartUp Hiring Substack for deeper dives, tools, and real stories you won’t hear anywhere else.

  1. 06/03/2025

    StartUp Hiring #5 Erica Wass. Bad hires are a 2.5x salary burn.

    Scaling Product Teams with Zendesk's Former Director Erica Wass.In this episode, I sit down with Erica Wass, one of Australia's most respected product leaders and Former Director of Product at Zendesk. We dive deep into the art and science of building product teams that actually drive business outcomes.What we cover:The 3 C's every product manager must demonstrate (beyond technical skills)Why hiring the "perfect" PM might be costing you 2.5x their salaryHow to lead distributed product teams across impossible time zonesThe critical question every PM should ask before joining a startupWhy AI is happening FOR product managers, not TO themCommon mistakes startups make when hiring their first product teamKey insights:How remote leadership can create more authentic relationshipsWhy product managers need to be strategic, not just tacticalThe importance of treating hiring like product-market fit for candidatesHow to balance speed vs. quality in startup hiring decisionsErica brings over 15 years of product experience from companies like Bloomberg, Zendesk, and now as a consultant helping scale-ups build world-class product organizations. Whether you're hiring your first PM or scaling to 100+, this conversation is packed with actionable insights.Timestamps and links in the comments below.Timestamps:00:00 - Introduction and Erica's background03:15 - Evolution of product hiring across startup vs enterprise07:30 - The shift from feature factories to strategic product management12:45 - Balancing speed vs perfect hire in startup environments18:20 - The 3 C's: Capability, Customer Curiosity, and Communication23:10 - Leading distributed teams across time zones28:45 - The pizza call story: Remote leadership lessons32:20 - Common startup hiring mistakes and how to avoid them37:50 - Aligning product hires with founder expectations42:15 - The critical question PMs should ask before joining startups45:30 - Hiring retros and continuous improvement48:45 - How AI is changing product management52:00 - Closing thoughts and where to connectConnect with Erica on LinkedIn: https://www.linkedin.com/in/ericawass/

    38 min
  2. 05/22/2025

    StartUp Hiring James Dale - Joined Apple at 17 then sold a StartUp to Snapchat

    Navigating Startups: Insights from Moving to Apple at 17 and Founding a BusinessIn this conversation, James Dale shares his journey from a 17-year-old intern at Apple to founding his own business. He dives deep into the challenges of being a young founder, the importance of quality hiring, and the sheer amount of work required beyond one's main discipline. James reflects on the excitement and stress that comes with startups, offering valuable advice for anyone looking to join or start one. He also emphasises the evolving landscape of technology and the crucial role of customer feedback in product management. Whether you're a budding entrepreneur or a tech enthusiast, this episode is packed with insights on navigating the startup world.00:00 Meeting James Dale: The Early Days00:22 James' Journey to Apple00:35 Challenges of Being a Young Founder01:03 Moving to the US and Personal Growth01:53 The Apple Internship Experience03:25 The State of Tech Education04:54 The Role of AI in Tech Careers06:03 Founding a Consultancy Business08:08 The Reality of Startups12:15 The Importance of Good Hiring10:19 The Importance of Work Processes14:50 Meeting Efficiency Rules16:51 Onboarding New Hires19:45 Effective Feedback Strategies23:08 Hiring Mistakes to Avoid26:07 Advice for Aspiring Startup Employees28:25 Conclusion and Hiring AnnouncementsContact James:  / james-dale  https://fridaytechnologies.com.au/Welcome to StartUp Hiring — the home of better hires, better businesses, and better jobs.If you’re building a team or thinking about joining one, you’re in the right place.This channel is for founders, operators, and curious job seekers who want to get hiring right. Not just fast hires, good ones. Not just dream jobs, real ones. We talk to the people who’ve done it: early-stage founders who’ve made high-stakes hires, candidates who’ve landed roles without ticking every box, and teams who’ve figured out what works (and what doesn’t).Why? Because hiring is the highest-leverage thing you’ll do. And bad hires are expensive in every way.We dig into the how. How people are getting hired, how founders are building small, sharp teams, and how AI is changing the whole thing. If you're trying to level up your hiring or career (without the fluff), hit subscribe.Good people want to work for good leaders. And like attracts like.So the best hires don’t come from a clever ad or a flashy employer brands, they come from great clarity, process and teamwork. For more 🎙 Subscribe to the newsletter: https://readstartuphiring.substack.com/ 🌐 Visit the website: https://startuphiring.com.au/🔗 Connect with Simon on LinkedIn:   / simonstartuphiring   📘 Join the Facebook page:   / startuphiring  In and amongst creating this sort of content, I still personally help businesses to hire through my Talent Consultancy, Crew Talent Advisory. So if you need to hire one person or a whole team, hit me up for a chat.🌐 Visit the Crew website: https://wearecrew.io/I’ve been an in-house recruiter at Zendesk, MessageMedia and most recently at Cuttable. I’ve sat in the pods with teams doing the building, in interview rooms with hiring teams and on more video calls than I can remember.

    28 min
  3. 05/14/2025

    StartUp Hiring #15 Ben Mostafa - Engr to CTO in 10 years.

    When Ben Mostafa joined MessageMedia, he didn’t know what a CTO was. By the time he left, he’d been one. Over nearly ten years, he helped grow the company through different phases of scale, infrastructure-heavy tech, product-led SaaS, major user growth, and acquisitions. Along the way, he hired ICs and engineering leaders, built high-performing teams, and adapted his own leadership style.What I like about Ben’s perspective is how grounded it is. He’s technical, thoughtful, and clearly values people who take ownership, ask questions, and work well in ambiguous environments. The throughline in everything Ben shared was ownership. Whether you’re a new engineer or a senior leader, the people who thrive in startups are the ones who take responsibility for outcomes — not just tasks. They run toward problems, not away from them. “Your job won’t be what it says on the tin. Startups need people who can pick things up, get curious, and figure it out.”-----------------------------------------------------------------------------------------------------------------------------------------Welcome to StartUp Hiring — the home of better hires, better businesses, and better jobs.If you’re building a team or thinking about joining one, you’re in the right place.This channel is for founders, operators, and curious job seekers who want to get hiring right. Not just fast hires, good ones. Not just dream jobs, real ones. We talk to the people who’ve done it: early-stage founders who’ve made high-stakes hires, candidates who’ve landed roles without ticking every box, and teams who’ve figured out what works (and what doesn’t).Why? Because hiring is the highest-leverage thing you’ll do. And bad hires are expensive in every way.We dig into the how. How people are getting hired, how founders are building small, sharp teams, and how AI is changing the whole thing. If you're trying to level up your hiring or career (without the fluff), hit subscribe.Good people want to work for good leaders. And like attracts like.So the best hires don’t come from a clever ad or a flashy employer brands, they come from great clarity, process and teamwork. For more 🎙 Subscribe to the newsletter: https://readstartuphiring.substack.com/ 🌐 Visit the website: https://www.linkedin.com/in/simonstartuphiring/🔗 Connect with Simon on LinkedIn: https://www.linkedin.com/in/simonstartuphiring/ 📘 Join the Facebook page: https://www.facebook.com/startuphiringIn and amongst creating this sort of content, I still personally help businesses to hire through my Talent Consultancy, Crew Talent Advisory. So if you need to hire one person or a whole team, hit me up for a chat.I’ve been an in-house recruiter at Zendesk, MessageMedia and most recently at Cuttable. I’ve sat in the pods with teams doing the building, in interview rooms with hiring teams and on more video calls than I can remember.

    30 min
  4. 05/14/2025

    StartUp Hiring #15 Paul Perrett. Billion Dollar Exec talks about hiring.

    $3bn +. That's the deal value that Paul Perrett has overseen as a leader, making him without doubt one of Australia's most successful B2B SaaS leaders. In this video, you'll learn how Paul thinks about the power of hiring the right people, why he still thinks that people are the number one asset of any business and how his approach to hiring and leading has evolved over the years.Paul’s perspective is built on reflection. He’s done the work. He’s made hiring mistakes. And he’s honest about what it takes to build trust in small teams, how leadership changes over time, and why clarity about goals, fit, and style matters more than everPaul is a leader who’s not afraid to jump in, get his hands dirty, and unblock his team when it counts. But he also knows when to step back and let others lead.“There’s nothing more powerful than quietly unblocking something for someone, even if no one else sees it.”That sort of leadership builds trust. It’s not loud. But it compounds.-----------------------------------------------------------------------------------------------------------------------------Welcome to StartUp Hiring — the home of better hires, better businesses, and better jobs.If you’re building a team or thinking about joining one, you’re in the right place.This channel is for founders, operators, and curious job seekers who want to get hiring right. Not just fast hires, good ones. Not just dream jobs, real ones. We talk to the people who’ve done it: early-stage founders who’ve made high-stakes hires, candidates who’ve landed roles without ticking every box, and teams who’ve figured out what works (and what doesn’t).Why? Because hiring is the highest-leverage thing you’ll do. And bad hires are expensive in every way.We dig into the how. How people are getting hired, how founders are building small, sharp teams, and how AI is changing the whole thing. If you're trying to level up your hiring or career (without the fluff), hit subscribe.Good people want to work for good leaders. And like attracts like.So the best hires don’t come from a clever ad or a flashy employer brands they come from great clarity, process and teamwork. 🎙 Subscribe to the newsletter: https://readstartuphiring.substack.com 🌐 Visit the website: https://www.startuphiring.com.au 🔗 Connect with Simon on LinkedIn: https://www.linkedin.com/in/simonstartuphiring 📘 Join the Facebook page: https://www.facebook.com/startuphiring In and amongst creating this sort of content, I still personally help businesses to hire through my Talent Consultancy, Crew Talent Advisory. So if you need to hire one person or a whole team, hit me up for a chat. https://wearecrew.io/I’ve been an in-house recruiter at Zendesk, MessageMedia and most recently at Cuttable. I’ve sat in the pods with teams doing the building, in interview rooms with hiring teams and on more video calls than I can remember. You can get me at simon@startuphiring.com.au or 0459 59 22 01

    33 min
  5. 05/09/2024

    StartUp Hiring # 14 Dan Mottau. Better hiring through better leadership

    Welcome to Start, Scale, Grow - the ultimate destination for technology companies looking to level up their hiring game. Whether you're just starting out or well on your way to becoming a major player in your industry, we've got you covered. In each episode we'll bring you insights and actionable tips from the people who’ve done it, to help you find, hire and retain the best talent possible in the competitive world of tech. We've all heard the saying that good people want to work for good leaders and that like attracts like. Ask any recruiter or talent acquisition pro and they'll be able to tell you about times when candidates have gushed about how good a hiring manager is when debriefing after an interview. Good quality leaders help you thrive by not just being good at their individual jobs but also because they build high-performing teams, and that's what we all want right?In this episode, I chat to Dan Mottau who has extensive experience in developing and coaching leaders. His insights are brilliant and watch out for the moment when I tell him that this episode was better than I expected 🤣Find Dan here https://www.linkedin.com/in/danmottau/ Big ticket items: 2:23 The difference between leadership and management - the conflation. Procedural elements = management. Living personal values & how you show up = leadership 5:00 Being a leader of yourself. Start there. Lead yourself, lead a team, lead a business. 11:00 Many organisations are playing catch-up when it comes to leadership. We often promote people to leadership roles and then train them, not the other way around. 13:30 The terror of running your first one on one. 15:09 The sense of reward and recognition is different between an I/C and a leader. Immediate vs delayed. The feedback loop is longer. This doesn’t sit well with our brains. 18:10 The best leaders create the conditions of success. 21:14 The power of the silent achiever - does aspiration for leadership equate to leadership quality. It’s up to the individual to express and show their values to the business. Whether it’s overtly or otherwise. 25:44 Our careers are ours to own - a football coaches wisdom, transfers to the business world. 27:15 Dan gets asked, “how can I be more extroverted?” frequently. He talks about leveraging your own “superpower”. 31:10 Leaders attract or repel great talent. People always ask “whats in it for me?” when changing jobs. The number one answer to that is great leadership and growth opportunities. 33:10 Your direct manager/leader has more impact on your mental health and well being than your partner! Intuitively we know this, so the responsibility is on companies to think deeply about the quality of leadership they both hire and develop. 35:30 The capabilities and strengths of a great leader pre-covid are no different to know. The difference is that you can’t fake it when you operate in a hybrid or remote setting. In person you can hide behind charm and charisma. This can’t really be done at distance. 41:15 Do companies invest enough in developing their leaders? 43:30 “The forgetting curve is brutal” - our brains can only take so much information. Dan explains. 47:10 The best sporting teams have a sporting philosophy and hire to that philosophy. This means that the team doesn’t fall apart when a key player leaves, because the philosophy remains. This also breeds high-quality succession plan. 55:00 Dans reaction to “this was better than I expected” 🤣------ Social ------💡 Crew Blog » https://wearecrew.io/blog/🏆 Carrer Page Awards » https://wearecrew.io/the-alfies/Regardless of where you are on your journey, we can help. https://wearecrew.io/contact/👍 Facebook » @CrewTalentAdvisory🦜 Twitter » @WeAreCrewTalent👩‍💼 LinkedIn » Crew Talent Advisory

    56 min
  6. 04/15/2024

    StartUp Hiring #12 Cameron Nott. Understanding people is the key to success.

    In all walks of life, trends drift in and out of popularity. Recruiting is no different. For years, personality profiling was a large part of many companies hiring processes. As the battle for talent got fiercer, hiring time became more important. Companies needed to move quickly for in-demand talent that had plenty of options. Personality profiling started to become seen as a friction point, something that slowed competitive processes down. But there seems to have been a resurgence of interest in this space over the last few years. The rise of remote and hybrid teams has forced many companies to rethink how they go about hiring but also how they better understand the people who join them. Leaders have needed more tools and personality profiles are increasingly being (re)seen as a way to do this.I spoke with the Managing Director of The Myers-Briggs company in Asia Pacific to learn more about personality and cognitive assessments and their use.3:26 - The MBTI is about giving people a language and model around personality types so that we can better understand each other and ourselves.6:40 - Mitigating the risk of poor hires. Some people just interview well and sometimes the pressure of hiring quickly can impact quality. Profiling can help you make the best decisions possible. It can validate what you think you already know or open the door to some other avenues to consider.8:55 - Balancing our own Some people interview well but then again some don’t. Profiling can help mitigate bias and level out our perceptions of a candidate away from the interview room. 11:14 - Cognitive ability & Cognitive agility. Cameron explains the differences and what they actually mean. 12:40 - Timing. Cameron shares his thoughts on the best time in the hiring process to run profiling? 15:14 - Training. Bringing the capability in-house, training your own people to use the tools. 20:40 - Post Covid. Have client's requests changed in a Post Covid world due to remote and hybrid working? Some assessments can uncover the amount of sociability someone might need for example. 25:10 - Onboarding - Including assessment feedback as part of the onboarding process can help build trust, identify opportunities for development and highlight strengths. 27:10 - Discussions around Psychological Safety have increased over recent years. Personality profiles can help develop this in a remote/hybrid work setting by better understanding people and teams. 29:00 - The loss of incidental interactions that remote/hybrid work has brought us can impact psychological safety. Purely transactional dialogue can be draining. 31:15 - There’s a danger of over-reliance on subjective decision-making. This is why gathering as many data points as possible is so important. 34:05 - Building high-performing teams, leaders might need to think about what else they can be doing to build more trust in their remote/hybrid teams. 37:40 - Furry Invasion. My cat drops in to say hi and looks very happy to be there.36:45 - Employee surveys - learning and development is high on the list, profiles can help develop these opportunities. Find Cameron on LinkedIn -   / cameronnott  Some Myers-Briggs reading on high-performing teams - https://au.themyersbriggs.com/themyer... 🔔 Subscribe for more Talent Acquisition & HR insights like this: http://bit.ly/3sKF2rC

    38 min
  7. 12/13/2023

    StartUp Hiring #11 Jason Atkins. Demystifying Equity.

    In this episode, Jason Atkins the Co-Founder and President of Cake Equity shares his insights and demystifies the world of staff equity. From tax breaks to staff engagement, there are so many benefits to doing this, and it's not as difficult as you may think.Cake is 5 years old and has over 150k equity holders on the platform in 80 different countries. They're the definition of an Aussie tech success story. The big ticket items 👇🏻2:15 - what is equity? A term for the ownership of a company.6:15 - the impacts on founders of going down the equity share route. Founders technically own less, but the flip side is that they can attract, engage and retain better people and teams. 9:43 - The impact on strategy and culture of equity ownership. Founders need better tools for managing this. 13:55 - There are two types of value in employee ownership. The cash value, and also the day-to-day value. The alignment between leadership and employees who are working together to build brilliant products and companies.16:30 - There are clear productivity gains in employee-owned businesses over more traditional business models.18:15 - Clarifying the terms “Vesting period” and “Cliff”.21:14 - There are tax implications to this. Employees NEED TO DO THEIR OWN CHECKING.21:49 - Offering shares/options to international employees. A way to fully embrace the distributed team model. There can be complications for both the employer and the employee, but it is possible. (Luckily Cake can help with this 👍🏻)25:10 - Why wouldn’t a business go down this path? There are cultural and business inputs needed, it needs to be a part of your day to day culture. If this isn’t for you, then don’t do it. 26:30 - Startups, under 7 years old have some clear tax advantages to doing this, so it makes sense. Older businesses dont have this and there can be complications around going down this route.28:19 - The difference between RSU (Restricted Stock units) and Options. Established businesses generally go down the RSU path, Start Ups go with options.31:40 - This isn’t as hard to roll out as people may think. Thanks to Cake 🍰 Pretty much every ESOP plan they’ve seen has been incomplete in some way.34:43 - The organisational debt around trying to do this manually carries too much risk. 🤯 The Cake platform removes this debt, so why wouldn’t you? (Shameless plug 👍🏻)🔔 Subscribe for more Talent Acquisition & HR insights like this: http://bit.ly/3sKF2rC------ Social ------💡 Crew Blog » https://wearecrew.io/blog/🏆 Carrer Page Awards » https://wearecrew.io/the-alfies/Regardless of where you are on your journey, we can help. https://wearecrew.io/contact/👍 Facebook » @CrewTalentAdvisory🦜 Twitter » @WeAreCrewTalent👩‍💼 LinkedIn » Crew Talent Advisory------ Crew Talent Advisory ------We have a range of recruitment services to suit any stage of your business’s evolution because humans aren’t a one-size-fits-all kind of deal (if they were there’d be no need for adjustable baseball caps)------ Customer Testimonials ------🎬 MessageMedia: https://youtu.be/JlRl9yuTaCg🎬 Xplor: https://youtu.be/vObszKdYsDQ🎬 Ippon: https://youtu.be/-Wp4fgxHaRE

    38 min

About

StartUp Hiring is a podcast about what really happens when startups grow, through the people they bring in. Each episode features someone who’s lived it: founders making early hires, operators landing roles, and people building careers inside startups. We dig into what worked, what didn’t, and what they’d do differently. If you're building a team or trying to join one, this is for you. Subscribe to the StartUp Hiring Substack for deeper dives, tools, and real stories you won’t hear anywhere else.