40 episodes

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.

BreakOut Podcast by OutScout - tech talent matching for mission-critical hires

    • Business
    • 5.0 • 3 Ratings

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.

    39 | Adapting GTM for SaaS Transformation - Ernie Hu @ CAST Software

    39 | Adapting GTM for SaaS Transformation - Ernie Hu @ CAST Software

    SUMMARY

    In this episode of the Breakout Podcast, Ernie Hu, who holds a hybrid role of CRO and COO at CAST, shares his extensive experience in the software industry spanning three decades, including 20 years at IBM. 

    Hu discusses CAST's journey to become the go-to name in software intelligence, referring to it as the MRI for software. He elaborates on the challenges and strategies of transitioning to a SaaS subscription model and the importance of specialization in sales. Hu emphasizes the need for alignment within teams and clear communication from leadership for successful execution. He also reflects on the fresh perspectives brought by private equity ownership and offers advice for aspiring Chief Revenue Officers. 

    The conversation highlights the evolving sales culture and operational dynamics within a fast-growing, private equity-backed software company.



    Timestamps:

    [00:00:00] Defining and Leading a New Category [Cold Open]

    [00:00:45] Welcome to the Breakout Podcast

    [00:01:17] Meet Ernie Hu: Career and Role at CAST

    [00:01:52] Understanding CAST: The MRI for Software

    [00:04:57] Sales and Market Dynamics in the SaaS World

    [00:05:20] Specialization and Sales Strategy at CAST

    [00:13:09] Evolving Sales Culture and Compensation Plans

    [00:20:22] Private Equity Influence and Business Evolution

    [00:27:12] Leadership Insights and Final Thoughts



    Listen to the Breakout Podcast: Apple|Spotify

    Let us know what else you’d like to hear & see covered: contact@outscout.io

    Connect with Gareth - https://www.linkedin.com/in/gareth-webb-outscout/ 

    Connect with Ernie - https://www.linkedin.com/in/ernie-hu-6b06a4129/

    See how OutScout can help you smash your hiring goals - https://www.outscout.io/

    • 36 min
    38 | A-Player Attraction: Stand-out Tactics with Taylor Robinson @ Searchworks LLC

    38 | A-Player Attraction: Stand-out Tactics with Taylor Robinson @ Searchworks LLC

    In this episode, Gareth Webb sits down with Taylor Robinson - President of Searchworks LLC, an executive search company. Tune in for insights on ways you can increase your efficiency in attracting top talent, AI’s place in recruitment, and creating a white glove post-hire onboarding experience.

    TIME STAMPS

    02:00 Taylor’s background at Searchworks

    04:00 Market conditions in 2023 and its impact on search

    06:00 What lies ahead in 2024

    09:00 Ways to differentiate yourself when reaching out to top talent

    13:00 What you can do upfront to increase candidate attraction with a role

    15:30 Why you should consider video when crafting JDs

    18:30 Are you clearly answering “Why would someone want to work here?”

    21:10 AI’s place in recruiting

    28:30 Ensuring candidates have a successful first 90 days

    32:15 Acting as a logical partner with hiring managers to make the best decision

    36:00 What’s next for search/TA/staffing and how it fits into the future of work?

    40:30 Final note on AI

    42:00 Advice to those setting up a recruitment firm or team

    Listen to the Breakout Podcast: Apple|Spotify

    Let us know what else you’d like to hear & see covered: contact@outscout.io

    Connect with Gareth - https://www.linkedin.com/in/gareth-webb-outscout/ 

    Connect with Taylor - https://www.linkedin.com/in/taylorsrobinson 

    See how OutScout can help you smash your hiring goals - https://www.outscout.io/

    • 44 min
    37 | Navigating Hyper-Growth: Insights on Scaling from 10 to 160 - Dan Wang @ Iterative Health

    37 | Navigating Hyper-Growth: Insights on Scaling from 10 to 160 - Dan Wang @ Iterative Health

    In this episode, Gareth Webb sits down with Dan Wang - VP, Finance & Operations at Iterative Health. Tune in for insights on challenges faced when scaling rapidly, talent acquisition strategies, and advice for aspiring leaders.



    1:53 Dan’s background and growth at Iterative Health

    5:13 The 3 key benefits you get from business school and how that can impact your career

    7:53 Business school downsides

    9:03 Insights into the product and tech behind Iterative Health

    11:27 How business needs and employee skill set needs change when businesses grow headcount

    12:38 Executive level changes at below and above 80 employees

    14:28 Everyone’s a generalist - when should this change and the need for higher levels/managers come up?

    17:23 Three lessons learned as Iterative went through rapid growth

    21:28 Why a chief of staff should be considered in your business as early as Series A

    25:08 What tools and frameworks are used in MBA education

    27:53 What have you done well to attract top-tier senior talent?

    30:15 What do you do when you decide networks don’t cut it and you need to go outside help?

    32:23 When should you decide to build out an internal TA team?

    33:23 How to build out successful onboarding when you 3X headcount

    34:43 How junior do you typically hire and how does that change as the company grows

    37:23 Making hybrid work models meaningful for in-person interactions

    43:38 Advice to ICs aspiring to get to VP

    47:23 Recommended resources for continuous learning



    Listen to the Breakout Podcast: Apple|Spotify

    Let us know what else you’d like to hear & see covered: contact@outscout.io



    Connect with Gareth - https://www.linkedin.com/in/gareth-webb-outscout/ 



    Connect with Dan - https://www.linkedin.com/in/danwang11/

    See how OutScout can help you smash your hiring goals - https://www.outscout.io/

    • 49 min
    36 | Exploring Today's Startup Landscape: Fundraising, Labor Markets, and Strategic Advice from Monica Driscoll @ SVB

    36 | Exploring Today's Startup Landscape: Fundraising, Labor Markets, and Strategic Advice from Monica Driscoll @ SVB

    Exploring Today's Startup Landscape: Fundraising, Labor Markets, and Strategic Advice from Monica Driscoll @ SVB

    In this episode, Gareth Webb sits down with Monica Driscoll to discuss the current startup fundraising landscape, labor market, and advice for founders looking to raise. 

    Listen to the Breakout Podcast: Apple|Spotify



    Let us know what else you’d like to hear & see covered: contact@outscout.io

    Connect with Gareth

    https://www.linkedin.com/in/gareth-webb-outscout/ 

    Connect with Monica

    https://www.linkedin.com/in/monica-driscoll-83b850a2/

    See how OutScout can help you smash your hiring goals - https://www.outscout.io/

    • 42 min
    35 | Scout this: Engineering Manager @ Growth Stage LegalTech Startup

    35 | Scout this: Engineering Manager @ Growth Stage LegalTech Startup

    In this episode of Breakout's mini-series, "Scout This," Gareth and Jake dive into a company's open position for an engineering manager. They discuss the importance of understanding the current problems and future goals of the business, as well as effectively communicating these to potential candidates. The hosts also touch on the market's improvement and the need to build teams confidently. Tune in to gain insights on best practices for hiring and building successful teams.

    [00:02:00] AI-powered legal tech company.
    [00:04:11] Technology for justice and equality.
    [00:09:21] Data-heavy generative AI infrastructure.
    [00:12:08] Open roles and team information.
    [00:17:29] Years in company and qualifications.
    [00:22:23] A well-constrained search.


    Listen to the Breakout Podcast: Apple|Spotify
    Let us know what else you’d like to hear & see covered: contact@outscout.io
    Connect with Gareth - LinkedIn
    Connect with Jake - LinkedIn 

    See how OutScout can help you smash your hiring goals - https://www.outscout.io/

    • 25 min
    34 | Scout this - Senior Product Manager @ Series B AI Healthtech

    34 | Scout this - Senior Product Manager @ Series B AI Healthtech

    In this episode of Breakout, Gareth Webb and Jake Gorgol discuss the importance of considering years in the current company when evaluating potential candidates. He shares his approach of looking at candidates who have been with their company for two or more years, narrowing down the pool to 144 individuals. Gareth then dives into a specific job opening for a senior product manager position at Mendel AI, a company focused on using AI to parse complex patient data. They provide insights into the company's recent funding and expansion plans. Tune in to get valuable tips on building teams more confidently in the early growth stages of a company.

    [00:00:53] Scouting Potential Product Managers
    [00:05:39] Complex healthcare data experience.
    [00:08:00] In-office work limitations.
    [00:09:43] Remote work and top talent.
    [00:14:44] Senior PMs at data-heavy companies.
    [00:17:27] Hiring for niche healthcare data.


    Listen to the Breakout Podcast: Apple|Spotify
    Let us know what else you’d like to hear & see covered: contact@outscout.io
    Connect with Gareth - LinkedIn
    Connect with Jake - LinkedIn 

    See how OutScout can help you smash your hiring goals - https://www.outscout.io/

    • 19 min

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