Executive Leadership Development — Keith Street Advisory

Fit

Who this is for.

Companies roughly between $5M and $50M in revenue, typically:

Founder-led or family-owned, growing faster than the management structure
First-time managers who were promoted on technical strength
A leadership team that's never had structured development
Turnover in the layer just below the executive team
A founder who needs to delegate but has no one ready to take it
No succession plan for key operating roles

I work with logistics, distribution, manufacturing, and transportation companies most often, because that's where I can add industry context on top of the leadership work. But the leadership problems are close to universal, and I take clients outside those sectors.

Services

What I actually do.

One-on-One Executive Coaching

Direct, confidential work with a specific leader — a founder, a new VP, a manager who's struggling or who's about to be handed much more. Typically biweekly over three to six months.

Leadership Team Development

Working with your management group as a unit: how they make decisions, hold each other accountable, communicate through the layers, and handle conflict without routing everything through the founder.

New Manager Foundations

Structured development for people promoted on individual performance. Delegation, accountability conversations, coaching their own people, running a meeting worth attending, and managing former peers.

Succession & Bench Building

Identifying who has capacity for more, building individual development plans against real roles, and creating internal promotion paths. I built exactly this at XPO — fourteen participants in a formal development program, five promoted into Director and VP roles.

Sales Leadership Development

A specialty, given where I came from. Pipeline discipline, forecast accuracy, coaching to behaviors rather than results, territory design, and the transition from top producer to sales leader — which fails more often than any other promotion in business.

Approach

I'm not a certified coach, and I won't pretend the credential is what matters.

What I bring is having actually done it. I've led 2,400 people across six states and Puerto Rico. I've turned around an underperforming region. I've cut turnover 68% by changing how leaders led rather than by changing the leaders. I've had five direct reports promoted to Director and VP. I've had the hard conversations, made the wrong calls, and learned from them in real operations where the results were measured every week.

I also started this career as a driver, alone in a truck at three in the morning, and I have not forgotten what it feels like to be led badly by someone who has never done the job. That is the single most useful thing I bring into a room full of new managers.

My philosophy is servant leadership, and I hold it because it produced better numbers than the alternatives — not because it sounds good on a website.

Three programs

What you can buy.

Sold as defined programs, not by the hour. Development takes a defined arc, and metering it by the session works against the result.

90 days · $7,000

New Leader Accelerator

$7,000

A structured 90-day arc: month one, leading yourself — time, priorities, and how you're perceived. Month two, leading the team — delegation, one-on-ones, accountability conversations. Month three, leading the business — metrics, executive communication, managing upward.

Includes a leadership assessment, six 60-minute sessions, a written development plan, a one-on-one and delegation framework, access between sessions, and a closing review.

First-time managers, new directors, operations managers, and high-potential employees.

6 months · $12,500

Sales Leadership Accelerator

$12,500

Your best salesperson shouldn't have to learn leadership by failing at it. Pipeline discipline, forecast accuracy, coaching to behaviour rather than results, running a sales meeting worth attending, strategic account strategy, executive selling, CRM discipline, hiring, and performance management.

Includes a full assessment, twelve 60-minute sessions, an individual development plan, an accountability framework, between-session support, and quarterly reviews.

Salespeople promoted into sales leadership, and the executives who manage them.

12 months · $22,500

Executive Advisory Retainer

$22,500

Rather than coaching one person, I'm available to you and your leadership team. Organisational structure, leadership challenges, sales strategy, operations, accountability, strategic decision support, and executive communication.

Two sessions monthly, ongoing advisory access, quarterly reviews, and an annual development plan.

Business owners, founders, and C-suite leaders.

Also available: half-day team sessions at $1,500 and full-day leadership intensives at $2,500 for management groups. Travel and lodging billed at cost.

You promoted your best people. Nobody taught them how to lead.