One-on-One Coaching, Strategic Advisory, and Chief of Staff Support for Leaders

Bring us thorny problems. We'll ask you really good questions. Together we'll find a hypothesis for what to try first.

Hypothesis Department's one-on-one coaching support around how to iterate your strategy, grow your team, and build your internal decision-making processes at your customer-led company is ideal for leaders who are:

Facing many opportunities and needing a way to break them down into chunks and choose the highest ROI options
Still needing to wear a lot of hats, make a lot of decisions, do everything completely (or mostly) on your own
Working solo or with a tiny team, especially founders who have found that going from a team of 1 to a team of 2 or more is nearly quadrupling the amount of communication and strategy challenges
Realizing that your solo processes of "observe an opportunity, build something to fix it, ship it" now has a few extra steps called "talk to team member about opportunity" and "find a way to communicate a vision without being overbearing"
In need a sounding board or rubber duck that can speak back to you
In need of a space to be vulnerable about what isn't going well

The outcomes we'll work toward: growth for your business and growth for you

Our work will start on your business's most painful pressing problems at the inflection point you're at today - whether that means making a new hire, discovering a new market, or realizing that you don't really understand your customers.

Your version of "what's next?" might look like:

"What's my next strategic decision?"
"How do I prioritize these great opportunities?"
"Who do I hire next when I want to hire everyone?"
"How do I invite my team members to collaborate while still preserving my vision?"
"Process? It was just me for so long, how do I even figure it out?"
"Blurgh blop everything that worked 3 months ago stopped working today, what do I do?"

Or something else altogether.

We'll start with identifying ways to answer those questions and building strategies to take advantage of those opportunities. And in doing that, we'll also identify ways for you to get better at understanding how to answer those questions on your own so you can operate more effectively tomorrow, no matter what hat you're wearing.

Why work with Alli?

Over the last 10 years I've helped over 50 software teams get to their next milestone - or throw out their old list of milestones to define a new set of milestones and launch a strategy more in line with their goals.

I've worked as a copywriter, experience designer, researcher, facilitator, and strategist with marketing, product, growth, PR, and customer success teams. It's true that this cross-functional experience has given me insight into the struggles you'll bump into across your customer-facing teams. It's more true to say that the skill I've cultivated over the years is the skill of figuring out how to navigate those struggles. What questions should we ask to get from where we are to where we want to go? That's where we'll work and play.

"I was crafting the strategy and plan for my client to achieve their growth goals, but as a strategist, I could tell that something was missing or off. It was like there was a missing puzzle piece that I couldn't quite identify or articulate. I was also having a hard time extracting the information I needed from the CEO and founder to help us fit the pieces together to chart our best path forward. Our session with Alli was the breakthrough I was looking for. Not only did she pull out so much more insight around what we needed to be successful, but she revealed some assumptions and requirements that weren't as clear or completely unknown before the session. The first big a-ha moment was that we had an opportunity to realign the client's efforts with the founder's vision. And the second a-ha moment is that without Alli's thorough questioning and unpacking process, we wouldn't have arrived at our conclusions about what to do next (and I would have still been left scratching my head wondering what I was missing)." -Asia Orangio, Founder of DemandMaven, Board Member at Moz

Sound fun? Pick one of 4 formats to get started

What weighs heaviest on your mind right now? Which of the many choices before you is the best path forward? You bring your thorniest questions, your most complicated emotions, your biggest doubts, and we'll suss out the blockers, the insights, and the highest ROI path forward.

Choose from three formats or blend them together:

A 2-hour Strategy Session: Great for sorting through one well-defined, tightly-scoped problem.
A Half-Day Deep Dive: Great for big questions with lots of tentacles, especially ones where you don't even know what the question is yet.
6 Months of Ongoing 1:1 Working Sessions: Great for when you or your team are growing, what worked last week doesn't work this week, and you're starting to sense that what got you here won't get you there.
6 months of Embedded Chief of Staff Capacity and Team Coaching: Great for when you need an embedded team member supporting you in advancing strategic initiatives and coaching you and your team on an ongoing basis.

Not sure where to start? We'll figure it out together.

Schedule a 30-minute meet-and-greet call to see if we're a fit

We'll schedule this first call to make sure there's a good mutual fit. You'll get a chance to see what it's like to have me ask you a few questions and to see if you'd like to do more of that. I'll get a chance to understand a little bit about your business to make sure I can help you reach your next milestone.

If it's a fit, we'll decide which format to start with.

If it's not, we'll have had a fun conversation.

Either way, how cool, right?? I can't wait to meet you. Book here and we'll talk soon. 👇

"The experience of working with Alli is like collaborating with a trusted friend." -Claire Suellentrop, Co-founder Forget the Funnel, Elevate, & Userlist