Strategic Partner Retainer

$1,000.00

The thinking partner your leadership role doesn’t include.

A monthly retainer for founders and leaders who are making significant decisions without a strategic peer in the room. OOTS doesn't run your operations — you do. What we bring is the framework, the hard questions, and the outside perspective that help you make better decisions, build stronger systems, and lead with intention instead of reaction. You bring the business knowledge. Together you build the strategy. You implement it.

Best For: Clients actively building or scaling who need a consistent operations and strategy partner.

What You Receive: Shared dashboard, 2 monthly strategy calls, async communication throughout the month.

Frequency:

The thinking partner your leadership role doesn’t include.

A monthly retainer for founders and leaders who are making significant decisions without a strategic peer in the room. OOTS doesn't run your operations — you do. What we bring is the framework, the hard questions, and the outside perspective that help you make better decisions, build stronger systems, and lead with intention instead of reaction. You bring the business knowledge. Together you build the strategy. You implement it.

Best For: Clients actively building or scaling who need a consistent operations and strategy partner.

What You Receive: Shared dashboard, 2 monthly strategy calls, async communication throughout the month.

Scenarios

Maya, 38
Owner of a 7-person interior design firm — the bottleneck in her own business

The situation

After her Clarity Session, Maya knows she's the problem — she just doesn't know how to fix it. Every decision still lands on her desk. She needs someone who will ask the hard questions monthly, hold her accountable to the changes she says she wants to make, and help her think through what to delegate and how. She has to do the work. She just can't do it alone.

What she gets

Each month, Abby asks what changed, what didn't, and why. She provides frameworks for delegation, decision-making, and team structure — Maya adapts them for her own business and implements them with her team. By month four, Maya has built the systems herself. They actually stick because she owns them.

Lilly, 45
Executive Director of a 12-person nonprofit — board-managed, staff-led, stretched thin

The situation

Lilly has a board that wants strategy and a staff that needs management — and she's the only person sitting between both. She doesn't need someone to write her grant narrative or manage her team. She needs a monthly thinking partner who understands operational complexity and will push back on her thinking before she takes it to the board.

What she gets

Abby helps Lilly prepare her own board presentations, develop her own staff performance approach, and build her own grant strategy — by asking the questions that stress-test her thinking before the stakes are high. Lilly does the work. Abby makes sure the work is the right work.