SaaSy Talk S01.19: The Challenges of Hiring the First Sales Leader in a Startup

About The Guest(s): Helping founders build out their GTM strategies and teaching sales reps how to earn the right to ask questions, which questions to ask, and when is the primary driver for Richard. He brings 20+ years of experience, having done all the roles, SDR, AE, Manager, Director, VP of Sales, and Director of Sales Ops to the table. His client list includes Fortune brands as well as start-ups, including Zoom, Salesforce, Human Interest, Dusty Robotics, Gainsight, and more. He's also the co-founder of Surf and Sales as well as the host of the Surf and Sales Podcast and his newest podcast, Sales Rants with Richard. He lives in Northern California with his wife, Cathy, sons, Riley and Bodhi, and two Cavapoos, Lola and Luna. Summary:Richard Harris discusses the challenges and benefits of remote work and the future of office work. He emphasizes the importance of trust between employers and employees and the need for open discussions about preferences and needs. Richard also shares his favorite sports team, music genre, and movies. Key Takeaways: The future of office work should involve open discussions about preferences and needs to find the right balance. Trust between employers and employees is crucial for successful remote work. Building a career can happen remotely, but it requires opportunities for real conversations and connections. Richard's favorite sports team is the Denver Broncos, and his favorite movie is Shawshank Redemption. Quotes: "There is zero trust between the employee and the employer. The employer doesn't trust the employee, particularly salespeople, to do their job, and they never have." - Richard Harris "The only way I ever see return to office happening in full is if we go through a really massive 2008 type recession." - Richard Harris "I'm a smooth guy these days. It's too fucking hard to spread the crunchy peanut butter." - Richard Harris ​Chapters:  00:00:28 Richard's early interest in sales and business 00:07:26 Richard's value and expertise recognized by clients 00:10:17 Defining a sales playbook: specific to use cases 00:12:30 Challenges of hiring the first sales leader 00:16:31 Hiring the first sales leader is a common mistake 00:19:45 Sales is often blamed for missed goals and unrealistic expectations 00:20:28 Difficulty in identifying true sales professionals 00:25:23 Importance of hiring stage-appropriate sales roles 00:31:40 Average tenure of sales leaders 00:37:00 The need for honest conversations 00:43:00 Richard expresses concern for employees with flexible work arrangements. 00:53:51 Quick fire round Subscribe on Spotify:  https://open.spotify.com/show/3ZVkJ12FIqD39oqgj7Kcjq  Subscribe on Apple:  https://podcasts.apple.com/us/podcast/saasy-talk-unfiltered/id1709426070 Subscribe on YouTube:  https://www.youtube.com/@SaaSyTalkUnfiltered Subscribe on Linkedin: https://www.linkedin.com/company/saasy-talk-unfiltered Subscribe to our Newsletter: https://substack.com/@saasytalkunfiltered Visit our Website:  https://saasytalkunfiltered.transistor.fm/  Follow Ricky Sevta on Linkedin:  https://www.linkedin.com/in/rickysevta/ Follow Sean Diljore on Linkedin:  https://www.linkedin.com/in/seandiljore/