Program 02

Mentorship from someone who's actually done it

Career, business, and executive mentorship in strategy, sales, marketing, business development, and leadership — with unlimited WhatsApp access between sessions so momentum never stops.

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Mentorship tracks

Choose your focus

Personal 1-on-1 Mentorship

A dedicated thinking partner for your goals — accountability, perspective, and a clear path forward.

Career & Professional

Career development, positioning, enterprise sales, and the soft skills that get you promoted and paid.

Executive Mentorship

For founders and leaders — strategy, global logistics, scaling teams, and decision-making under pressure.

See Digby's mentor profile & reviews →

Business Mentoring — 1 hour a month, unlimited WhatsApp

Plans from $125/month. Includes monthly 1-on-1 strategy sessions plus unlimited messaging support.

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Mentoring

What mentoring with Digby actually looks like

Most mentoring sounds good in theory. This is different, because it comes from someone who has actually run the operations, closed the deals, and led the teams. Digby R. Kerr spent more than thirty-five years inside global businesses like FedEx, UPS, XPO, and CEVA before he ever mentored a single client. When you sit down with him, you are not getting recycled advice from a book. You are getting a straight read on your situation from a person who has stood where you are standing.

Practical, not theoretical

Every session starts with what you are actually facing this month: a hard decision, a stalled project, a conversation you are dreading, or a career move you are weighing. Digby helps you think it through, then leaves you with clear next steps you can use the same week.

Support between sessions

Business does not wait for your next appointment. That is why every mentoring plan includes unlimited WhatsApp access. When something comes up, a tough email, a negotiation, an offer on the table, you can message Digby and get a fast, honest opinion before you act.

Built around you

A first-time founder needs different things than a mid-career manager or a senior leader preparing for the next level. Your mentoring flexes to fit your goals, your industry, and your stage.

How is mentoring different from coaching?

Coaching helps you find your own answers through structured questions. Mentoring adds direct guidance from someone who has already done what you are trying to do. With Digby you get both.

How often will we meet?

Most plans include a monthly one-on-one session plus unlimited messaging support in between. If you want to meet more often, that is easy to arrange.

Do you mentor people outside the United States?

Yes. Digby mentors professionals in more than twenty countries by video call, on a schedule that fits your time zone.

What if I am not sure mentoring is right for me?

Start with a free thirty-minute discovery call. No cost, no obligation, and you will leave with at least one useful idea whether or not you continue.

Book a free discovery call