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

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In 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 Rubrik

01:30 - Warm Outreach and Scalable Personalization

02:55 - From Cowboy to Tech Sales

05:33 - Why Ian Chose Tech Sales

06:15 - Moving to Austin Without a Job

06:57 - The Job Search Strategy That Wasn’t Working

08:19 - Targeting a Small List of Dream Companies

09:17 - Turning Unconventional Experience Into a Strong Resume

11:41 - How to Find the Best Tech Sales Companies

12:37 - Optimizing LinkedIn for Recruiters

13:44 - Why Storytelling Matters in Interviews

15:13 - The Cowboy Hook That Grabbed Interviewers’ Attention

15:59 - Overcoming the “Job Hopper” Objection

18:23 - Handling a Tough Final Round Question

20:05 - Studying Storytelling Before the Interviews

21:37 - How Ian Earned an Internal Rubrik Referral

24:25 - Building a Network Inside the Company

25:53 - The “45 7 Figure Earners” Interview Insight

27:12 - Researching Interviewers and Asking Better Questions

30:46 - Using Memorable Stories in Behavioral Interviews

32:41 - Preparing for the Mock Cold Call

35:06 - The Feedback That Proved He Was Ready

37:58 - Preparing the Prospect Presentation

39:17 - How Ian Closed Every Interview

42:21 - Why Rubrik Decided to Hire Him

43:10 - Training and Working as an SDR at Rubrik

45:32 - Building a Follow Up System

47:43 - Ian’s Long Term Career Vision

50:09 - Learning to Qualify the Right Prospects

52:12 - How Tech Sales Accelerator Helped

53:35 - Ian’s Final Advice: Bet on Yourself

ABOUT 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.

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