Aaron Ross: Author of “Predictable Revenue” and “From Impossible to Inevitable”

My Guest

Though Aaron Ross wears many hats, he is perhaps best known for co-authoring the global best seller Predictable Revenue, often referred to as “The Sales Bible of Silicon Valley,” which details an outbound prospecting system that’s created more than $1 billion across Salesforce.com and other companies. Most recently, Aaron published From Impossible to Inevitable, a book co-written alongside Jason Lemkin (serial tech entrepreneur, venture capitalist, and founder of SasStr.com, the world’s #1 resource for SaaS entrepreneurs), which is a “hypergrowth playbook” based on the successes of companies like Twilio, HubSpot, Marketo, and Salesforce.com.

In addition to being a sales advisor, board member, and highly sought after public speaker, Aaron also authors his own substack page, Fresh Air, where he focuses on the personal aspects of being a senior executive, including how to best manage anxiety, exhaustion, and stress, all of which are par for the course for substantially all entrepreneurs and CEOs.

Play The Episode

Listen in Your Browser:

Aaron Ross: Author of "Predictable Revenue" and "From Impossible to Inevitable" In The Trenches

Listen on Other Platforms:

Apple | Google | Spotify | Breaker | Pocket Casts | RadioPublic

Specific Questions and When They’re Asked

Managing Ones Self

  • (3:55) How vulnerable should CEOs be with their employees and other stakeholders? Should we shield others from our worries and anxieties, or should we “let others in”, so to speak?
  • (9:30) Tactically speaking, how can CEOs regularly “take off their armor”, and encourage others in the company to do the same?
  • (12:50) At a personal/emotional level, what are some of the similarities, themes, and patterns that you’ve noticed across your many years of working with entrepreneurs, CEOs, and other senior executives?
  • (20:30) What tactics, habits or routines do you use to manage and replenish your own energy?

The Roles that We and Others Play

  • (24:00) What advice would you give to sales leaders who feel like they can’t extricate themselves from the day to day? Can it possibly be as simple as hiring a manager to sit between them and their individual contributors?
  • (30:25) How involved should a CEO be in the sales process, particularly in the context of a small or medium sized business?
  • (35:00) You’re a proponent of specializing between hunters and farmers in a sales team. How do you do this for a team as small as two or three people? At what level of team size do you recommend differentiating between these two roles?

Lead Generation

  • (39:50) Is inbound marketing a “burnt out” tactic at this point? Even when prospects engage with an educational piece of content, are they not aware that they’re being explicitly marketed to?
  • (42:55) For leaders contemplating their relative mix of inbound vs. outbound lead generation, what questions that they should be asking of themselves and their companies?

Download a Written Transcript of Our Conversation

Access a text-based version of our discussion to highlight, copy or take notes by clicking on the button below

Subscribe and Never Miss an Episode

Subscribe wherever you enjoy podcasts:

Leave a Reply

%d bloggers like this: