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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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