#158 Cowboy To Rubrik SDR: Exactly how he broke into tech sales (with no experience) episode artwork

EPISODE · Aug 3, 2026 · 55 MIN

#158 Cowboy To Rubrik SDR: Exactly how he broke into tech sales (with no experience)

from The Chris Bussing Podcast [ Sell More | Live More ] · host Chris Bussing

Check Out RepVue →https://www.repvue.com/?utm_source=influencer&utm_medium=&utm_campaign=chris_bussing-Rubrik&utm_content=chris_bussingChat with me about 1-1 coaching: 👉https://calendly.com/bussingventures/session🎯 Free Cold Calling System →https://techsalesaccelerator.framer.website/🏢 Book me for corporate sales training & speaking →https://calendly.com/bussingventures/bussing-sales-speaking-training-consultIn this episode, Ian Cummings shares how he went from working as a cowboy on a 150,000 acre ranch to landing an SDR role at Rubrik with no previous tech sales experience. We break down the networking, storytelling, interview preparation and cold call strategies that helped him stand out, overcome tough objections and secure an offer at one of the world’s leading cybersecurity companies.Timestamps:00:00 - How Ian Booked 3 Meetings at Rubrik01:30 - Warm Outreach and Scalable Personalization02:55 - From Cowboy to Tech Sales05:33 - Why Ian Chose Tech Sales06:15 - Moving to Austin Without a Job06:57 - The Job Search Strategy That Wasn’t Working08:19 - Targeting a Small List of Dream Companies09:17 - Turning Unconventional Experience Into a Strong Resume11:41 - How to Find the Best Tech Sales Companies12:37 - Optimizing LinkedIn for Recruiters13:44 - Why Storytelling Matters in Interviews15:13 - The Cowboy Hook That Grabbed Interviewers’ Attention15:59 - Overcoming the “Job Hopper” Objection18:23 - Handling a Tough Final Round Question20:05 - Studying Storytelling Before the Interviews21:37 - How Ian Earned an Internal Rubrik Referral24:25 - Building a Network Inside the Company25:53 - The “45 7 Figure Earners” Interview Insight27:12 - Researching Interviewers and Asking Better Questions30:46 - Using Memorable Stories in Behavioral Interviews32:41 - Preparing for the Mock Cold Call35:06 - The Feedback That Proved He Was Ready37:58 - Preparing the Prospect Presentation39:17 - How Ian Closed Every Interview42:21 - Why Rubrik Decided to Hire Him43:10 - Training and Working as an SDR at Rubrik45:32 - Building a Follow Up System47:43 - Ian’s Long Term Career Vision50:09 - Learning to Qualify the Right Prospects52:12 - How Tech Sales Accelerator Helped53:35 - Ian’s Final Advice: Bet on YourselfABOUT ME:I help B2B tech companies build world-class outbound sales teams through training programs, workshops, and sales kickoffs. Former seller at Oracle, Google, & an AWS partner who has coached 100s of reps across the industry to hit quota & unlock their personal potential. »»» Subscribe for weekly tips to help you SELL more and LIVE more! «««

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#158 Cowboy To Rubrik SDR: Exactly how he broke into tech sales (with no experience)

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