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

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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.

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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?