
BreakOut Podcast
Welcome to the BreakOut Podcast. Tune in to stay up to date on all things tech talent, teams and trends through discussions with breakout technology leaders.
Latest episodes

Aug 15, 2023 • 24min
33 | Scout this - Head of Design @ Series A Ed-Tech
In this episode of Breakout Podcast on their 2nd Mini Series of Scout this. Jake Gorgol and Gareth Webb discuss the challenges of hiring designers and shared strategies for attracting top talent. Gareth emphasizes the importance of not limiting candidates based on specific experience but considering a range of skills and backgrounds.This episode also highlights the value of consistency in hiring practices. Tune in to gain insights on building teams confidently in early and growth-stage companies.[00:03:58] Low volume of applicants.[00:06:32] Lead the design strategy.[00:09:19] Addressing compensation and job requirements.[00:15:01] A good profile for targeting.[00:15:41] Inconsistency in sourcing methodology.[00:20:46] A focused list.[00:23:02] tips for average LinkedIn UsersListen to the Breakout Podcast: Apple|SpotifyLet us know what else you’d like to hear & see covered: contact@outscout.ioConnect with Gareth - LinkedInConnect with Jake - LinkedIn See how OutScout can help you smash your hiring goals - https://www.outscout.io/

Aug 1, 2023 • 36min
32 | Scout this - Marketing Manager @ Early-Stage Healthtech Startup
Welcome to Scout this - The first of our mini-series where we break down open positions and build out rough searches for growing early-stage companies that are currently hiring. In this episode, they discuss the challenges of sourcing and hiring for early-stage companies. They explore the difficulties companies face without a dedicated sourcing team and the importance of understanding the hiring process and attracting and retaining the right talent. Tune in to gain insights and best practices for building teams confidently in a startup environment.Want an open position scouted for your business? Send an email to contact@outscout.io for a chance to be featured! We’ll help to break down where you may not be getting traction and build out an initial search.Listen to the Breakout Podcast: Apple|SpotifyLet us know what else you’d like to hear & see covered: contact@outscout.ioConnect with Gareth - LinkedInConnect with Jake - LinkedIn See how OutScout can help you smash your hiring goals - https://www.outscout.io/

Jun 20, 2023 • 1h 12min
31 | The Inclusive Hiring Playbook: From Role Scoping to Fair Compensation - Jenn Gardner @ CharterUp
In this episode, Gareth Webb sits down with Jenn Gardner to talk everything about building successful teams - creating effective position definition & evaluation, promoting DEI in hiring, enhancing interviewing & assessment practices, and driving salary transparency and compensation alignment.CHAPTERS[01:20] Jenn’s background at CharterUp and prior experience[03:15] CharterUp’s unique value prop in the transportation market[07:06] Bringing people together - defining as culture vs community[10:00] What has Jenn done to counter “feeling on an island” [16:26] Defining and building out positions for critical hires[17:51] Every role gets a scorecard[21:07] The problem with job specs [22:33] Combating those opposed to setting up scorecards & putting in the upfront work[24:51] DEI - making the position more accessible to all types of talent[27:37] DEI - interview & assessment[31:02] Maintaining a consistent interview process to avoid biases[35:07] Live interview training[36:04] How to dig out actual performance from good interviewers[42:09] Salary/compensation transparency[45:01] Tools to help benchmark comp[54:37] Leading as an example and being clear with communications [01:01:23] Advice to founders regarding salary compensation and transparency[01:08.27] What is more difficult than it needs to be when it comes to hiring [01:10:19] Where to Connect with Jenn[01:11:12] Closing RemarksRESOURCES MENTIONEDPave - real-time compensation data - https://www.pave.com/ Carta - equity benchmarking - https://carta.com/ Gravie - benefits platform - https://www.gravie.com/ Listen to the Breakout Podcast: Apple|SpotifyLet us know what else you’d like to hear & see covered: contact@outscout.ioConnect with Jenn - LinkedInConnect with Gareth - LinkedInConnect with Jake - LinkedInSee how OutScout can help you smash your hiring goals - https://www.outscout.io/

Jun 6, 2023 • 51min
30 | From Offices to Open Spaces: Navigating Remote Work Trends - Gordon Smith @ HubbleHQ
In this episode, Gareth Webb sits down with Gordon Smith to talk about how to successfully navigate remote and hybrid work preferences, creating in-office time employees will value, and advice for early stage founders and team leaders in the remote work era. CHAPTERS[01:11] Gordon’s background responsibilities @ Hubble[02:40] Why Gordon joined - future of work[06:25] Companies working with Hubble[07:30] Hubble's "office" offering [09:29] Various trends & solutions[11:41] Differing views on hybrid company & executives.[14:23] Common theme among companies doing it well?[18:33] Do you think companies still like a “branded up” environment that is theirs?[22:01] What trends are you seeing?[23:56] Trends - mismatch in companies thinking they can get a good deal[27:53] What advice do you have for founders on office space[36:57] Making companies understand their data and its usage for an efficient solution[39:21] Has power shifted back to the employer?[40:46] What’s more difficult than it needs to be[47:07] Anyone we should have on the podcast?[48:47] Where to Connect with Gordon[49:29] Closing RemarksListen to the Breakout Podcast: Apple|SpotifyLet us know what else you’d like to hear & see covered: contact@outscout.ioConnect with Gordon - LinkedInConnect with Gareth - LinkedInConnect with Jake - LinkedInSee how OutScout can help you smash your hiring goals - https://www.outscout.io/

May 23, 2023 • 1h 3min
29 | Crafting your career: How to build a resume that sells - Gareth Webb on The Sales Syndicate Podcast
In this episode, Gareth Webb sits down with Jamie Pagan on The Sales Syndicate Podcast to break down five strategies you can use to help craft your career and your resume as you look for your next opportunity.TIMESTAMPS[04:24] Current market conditions (the negatives)[06:30] Current market conditions (the positives)[07:50] Companies overindulged [10:00] Why companies avoid hiring laid-off candidates & why it’s a mistake[14:00] Viewing interviews as pattern recognition[17:00] #1 - Importance of showcasing grit[23:30] Career strategy 101[26:30] #2 - Importance of documenting your success from day 1[33:00] How can you combat showing proof or evidence of success [37:10] #3 - Showcasing impact[48:00] #4 - Self-investment [59:00] Recap of resume buildersLink to the Sales Syndicate Podcast: Spotify|Apple Listen to the Breakout Podcast: Apple|SpotifyLet us know what else you’d like to hear & see covered: contact@outscout.ioConnect with Gareth - LinkedInConnect with Jake - LinkedInSee how OutScout can help you smash your hiring goals - https://www.outscout.io/

May 9, 2023 • 43min
28 | Building a Successful Remote Team - Insights from Adii Pienaar - Founder @ Cogsy
Join Gareth as he sits down with Adii Pienaar, a successful 3x founder who is currently building Cogsy, a cutting-edge e-commerce inventory and demand planning tool. Adii opens up about his incredible journey, sharing valuable insights and experiences in various aspects of entrepreneurship, including hiring and screening for top talent, building a remote team, and cultivating a strong and healthy culture.TIMESTAMPS[00:00:58] Adii’s background in e-commerce[00:05:53] Building a successful remote team pre-pandemic[00:09:53] Automatic’s acquisition of WooCommerce[00:13:11] Get intentional about culture and values from day one[00:15:37] Why a hybrid work model is hard to pull off[00:20:27] Why you should over-index on soft skills when hiring[00:27:54] The Cogsy team background[00:29:13] How to compete for talent outside of salary[00:31:55] The desire to keep building companies - when ego can be channeled positively[00:36:27] Advice for founders currently building[00:40:11] What’s harder than it needs to be when it comes to hiring?Listen on Apple | Listen on SpotifyLet us know what else you’d like to hear & see covered: contact@outscout.ioConnect with Adii - LinkedInConnect with Gareth - LinkedInConnect with Jake - LinkedInSee how OutScout can help you smash your hiring goals - https://www.outscout.io/

Apr 20, 2023 • 52min
27 | Hiring for Success: Insider Tips on Technical Recruiting - Stefanie Sher @ Replicated
In this episode, Stefanie Sher, Director of Talent Acquisition at Replicated, shares her insights on how to lead with credibility in a technical recruiting space, advice for hiring managers to avoid "bad practices," and how to influence them with data and cost-benefit analysis. She also discusses the current market landscape and the challenges of finding the ideal profile for hiring, especially in the context of diversity hiring. Stefanie also shares her favorite HR tech stack tools and discusses the role of AI in recruiting.

Feb 1, 2023 • 40min
26 | A CPO's Guide to Finding & Hiring Great Product Managers - Jonas Boli @ Phil
Joining us today is Jonas Boli, Chief Product Officer @ Phil - a Series D startup streamlining access to medications. In today’s episode, we dive into Jonas’ background at Zillow, his journey to CPO, what traits he looks for when hiring product managers and advice for aspiring CPOs.
[01:03] Jonas's Background
[02:20] About Phil
[08:45] Jonas’s longevity with Zillow
[12:55] Experience and benefits of working with Microsoft
[15:33] Jonas's move from engineering to product
[17:06] Key things you look for when hiring a product manager's
[19:25] Signals or red flags when hiring a product manager
[27:08] Standout traits of product professionals
[30:19] Advice for people aspiring to become CPOs
[33:50] Jonas's product trends predictions for 2023
[35:40] Team building practices to enhance productivity in 2023
Related Episodes
S1 E25 | Q&A hiring for small teams, tools to determine compensation ranges, getting creative with offers
S1 E24 | Talent strategies from midmarket and enterprise tech leaders - BreakOut live - Austin, TX

Dec 15, 2022 • 28min
25 | Q&A - Hiring for small teams, tools to determine compensation ranges, getting creative with offers
In this episode, Gareth Webb answers hiring questions including how to get started with a small team, compensation ranges, and being transparent on your company's unique value proposition.

Dec 8, 2022 • 1h 5min
24 | Talent Strategies from Midmarket and Enterprise Tech Leaders - BreakOut Live - Austin, TX
Tune into this recording (pt 2) from the very first BreakOut Live event hosted in Austin, TX this past May. Hear from talent acquisition leaders from LinkedIn, Dialpad, and Axon, what priorities they are focused on, and what they do to set themselves apart and compete for top talent.
Remember Everything You Learn from Podcasts
Save insights instantly, chat with episodes, and build lasting knowledge - all powered by AI.