The Most Important Pillars of Sales Leadership with Box’s CRO

A Conversation with Mark Wayland, CRO of Box

Mark Wayland is the Chief Revenue Officer of Box (NYSE: BOX), the cloud content management company that empowers enterprises to revolutionize how they work. Mark joined the FirstMark Guilds to discuss building robust sales organizations and successful sales leaders.

The Three Disciplines of Sales Leadership

  1. Selling skills: Selling is, of course, is the core function of the Sales org. To get promoted into sales leadership roles, you have to close deals. As you move higher up the ranks, you’re obviously not touching every transaction, but you’re engaged in major transactions for your organization.
  2. People skills: People skills encompass a variety of flavors including people management, emotional intelligence (EQ), coachability, and attracting talent. Great sales leaders make people want to be on their teams.
  3. Strategy & Operations: Strategy in sales means answering key execution questions like “What are our routes to market?” and “How do we manage the pipeline?”

While each bucket of skills is crucial to a successful Sales organization, individuals tend to only be great and one or two of these buckets. Oftentimes, you run into sales leaders who can close deals, but can’t scale or people don’t want to rally behind them.

The quick fix to this conundrum is to pair different types of leaders together (i.e.: a “rainmaker” and an “operator”) or make sures sales leaders are working in the function in which they shine.

On top of that, for those looking to become the most exceptional sales leader that they can, make it a point to deliberately develop mastery across all three of these pillars. When Mark went to Salesforce, for example, he believed had great selling and people skills, and that by working at one of the best-run sales organizations in software allowed him to learn Salesforce’s playbook and become a better operator.

A Strategic Shift from Rep Hiring to Rep Productivity

If you don’t successfully focus on ramping and retaining reps, you’ll be perpetually stuck short of the sales capacity you need (given the balance of ramped and unramped reps). This will leave you short of top line targets. And this challenge is only exacerbated by today’s extraordinarily competitive market for talent.

Great sales leaders have shifted sharply toward focusing on rep productivity and sales enablement. He shared three tactics he’s used to improve the rep productivity:

  1. Good hiring profile/onboarding programs: At Box, the team completely rebuilt the hiring profile so that recruiters and hiring managers know which competencies are particularly unique to Box and represented by top sellers. By using these screens, the company has hired much better candidates. Box also rebuilt their onboarding/enablement programs in the same spirit.
  2. Effective segmentation: Mark emphasizes that you need to give reps territories where they will be successful, instead of the “old school” way of giving top sellers total priority. Reps need to feel that the territories are balanced and equal to be productive and successful.
  3. Frontline management standardization: Mark likens the ideal standardization of your frontline management to that of the consistency of McDonald’s. The way frontline management operates across teams should be consistent (while still leaving latitude for leaders to lead in their own style.) This is key to decreasing the ramp time for reps. A few tactical examples:

Meeting cadence: Have a standard cadence for 1:1 meetings, team meetings, QBRs, account planning, etc. This may be slightly different across segments (ie: it’s a bit different in SMB and enterprise at Box), but should be standard across teams within a segment.

Framework: Box uses the MEDICC sales strategy framework, but just having a consistent framework across teams in general is important because it gives teams shared language and understanding.

Earning the Right to Drive Change as a New CRO

When Mark first arrived at Box, he received a lot of feedback and insights about what could make the Sales org and the company better. He made it a key priority to diligently listen to all these pieces of feedback. And just importantly, he needed to make sure his new team members felt heard, or else he would lose their trust as a new leader.

At the same time, he also knew he had to earn the trust of the entire executive team before pushing for any major changes. So over the course of his first year, he focused as much as possible on learning, listening, and executing under the company’s current framework. After this first year, he had earned the credibility, trust, and was armed with data to push for changes that he believed would accelerate the business.

Prioritizing the Right Changes

A similar vein in this conversation is knowing how to prioritize which changes to take on first. For Mark, this is the balance of two things: (1) the scale of the impact that a given change will make, and (2) the organization’s ability to implement and digest the change.

This latter element is something many leaders fail to take into account. One foundational framework for thinking through this piece of the equation comes from Mark’s work with HP, which defined organizational agility across three vectors:

  1. Time: how long with making this change take?
  2. Range: do we have the bandwidth to make this change?
  3. Ease: how much pain and friction will this put on the organization?

Knowing when, how, and whether to drive change will vary across companies and requires an intimate situational awareness of your organization. In Mark’s words, “People like change agents, but they only like people who break glass so much…”

The Key to Hiring Good Reps: The Interview Process

While Mark doesn’t interview reps very often anymore, he has a few tactics/questions he recommends frontline managers use in the rep interview process:

  1. Interview Chronologically: Start from someone’s educational history, step by step, and try to understand all the major decisions the candidate has made from then until now. It’s easy to hide problems in a LinkedIn world but a chronological interview allows you to uncover the candidate’s thought processes and former experiences.
  2. The Threat of the Reference: A favorite question of Mark’s is, “What will X say about you when I call them up?” This question usually drums up interesting responses and reveals information about the candidate’s past professional relationships, as well as speaks to how the candidate thinks of themselves.
  3. Test for Grit: Mark’s a big fan of Angela Duckworth’s book Grit and thinks the book is incredibly applicable to the field of Sales. Reps are constantly getting rejected and being thrown curveballs, so understanding how they persevere is crucial. To test for grit, I ask candidates about their former challenges/losses and how they approached them.

Are you a senior functional leader at a venture-backed tech startup? Apply here to join our Guilds. Members enjoy benefits including invites to private expert events, access to a full archive of playbooks and templates, inclusion in the private forum with other senior leaders, and much more.

To be eligible for Guild Membership, you must be a C- or VP-level leader at a technology company that has raised significant venture capital or grown to tens of millions of revenue.

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