Katie Roberts / Strategic operator
I find the gap,
build the system,
and get the right
people moving.
I connect what clients, teams, and the numbers are telling us, figure out where progress is breaking down, and turn it into a plan people can execute.
Strategy, with follow-through. Enterprise client work at Gartner is where I’ve put it to work.
$3.8M+ portfolio · $200K+ at-risk revenue recovered01 / How I operate
KatieOS
I work best where the problem is still a little foggy and everyone is using the same words to mean different things.
Creativity helps me connect things that don’t initially look related. Judgment is knowing which connection matters, what to test, and what to do next.
- 01
Read between the lines.
The first explanation is usually data, not the diagnosis. Look for the pattern, then ask what evidence would change the interpretation.
- 02
Connect the missing context.
Put the client signal, commercial stakes, and different teams’ perspectives in the same conversation. Find the decision everyone is circling.
- 03
Make the next move executable.
Name the owner, the action, and the next checkpoint. A QBR should not merely prove that a quarter occurred.
- 04
Build for the next time.
Turn useful moves into a repeatable process. Keep humans in the system and check whether the fix actually helped.
The pattern before the problem
Illustrative example / How I reason
Three clients ask different questions that somehow rhyme.
That’s a signal to investigate. Is the message unclear, is ownership missing, or is the next step too costly to take?
I’d compare the conversations and trace where progress stops. If the gap is the decision, I’d rebuild that touchpoint around an owner and an action, then watch what changes.
The repeated question tells me where to look. It doesn’t get to decide the diagnosis.
02 / Proof of impact
The commercial
stakes are real.
Selected results and scope from my work at Gartner as a Client Success Partner. The title describes the role; the examples below show the judgment, coordination, and systems behind it.
Portfolio scope and selected outcomes, not additive revenue totals. Engagement performance: #1 for engaged licensed users on my team; 9.52% unengaged, below the 10% North America top-decile threshold.
03 / Selected work
Find the gap.
Then do something.
The useful part is the connection between the problem, the choice I made, and what happened next.
Systems design · Information continuity
A good conversation should not need a full reboot two weeks later.
Agendas, recaps, and upcoming touchpoints held pieces of the same client relationship. I connected them into a living timeline so context could carry forward.
The judgment: treat the handoff between conversations as part of the operating process.
The goal was never more documentation. It was less re-explaining.
The system I built
- Custom visual agendas
- Connect the meeting to the wider client timeline.
- Post-call recaps
- Carry the discussion and next steps into the next touchpoint.
- Client timeline calendar
- Make upcoming conversations visible in context.
- Reusable prompt library
- Give recurring work a starting point that doesn’t begin from zero.
#1Engaged licensed users
on my team
on my team
9.52%Unengaged licensed users
below the 10% NA top-decile threshold
below the 10% NA top-decile threshold
Performance snapshot from the portfolio. These figures provide context; they do not isolate the effect of the timeline system.
Diagnostic judgment · Revenue recovery
Found the risk underneath the stated objection.
- The gap
- A renewal was at risk. The stated objection did not tell the whole story.
- My move
- Reframed the conversation around the decision leaders needed to make, then coordinated the evidence and stakeholders around it.
- What it demonstrates
- Diagnosing the obstacle, translating value into a decision, and getting the right people involved.
RECOVERED$200K+ at-risk revenue
Cross-functional execution · Commercial continuity
The org chart changed. The work still had to move.
- The gap
- An account executive vacancy affected roughly 30% of the territory.
- My move
- Stepped into sales cycles, account strategy, and executive conversations to keep commercial work moving across the vacancy.
- What it demonstrates
- Taking responsibility across role boundaries and coordinating around the client’s next decision.
SUPPORTED$650K+ renewal
04 / Systems in the making
Curiosity,
with a test attached.
I use AI and workflow experiments to make an idea concrete enough to question. The interesting part is deciding what the system should do, where it needs judgment, and what would count as useful.
VOID / Paused prototype
Can better questions change the next move?
A guided diagnostic flow that challenges the first explanation, offers an alternative, and ends with one concrete action.
The design problem: move from ambiguity to a useful experiment without pretending to know more than the inputs support.
The current web demo uses predefined branches and responses. It demonstrates the flow, not an adaptive AI diagnosis or a validated business outcome.
Explore the prototypeWorkflow design / Reusable guide
Build the handoff into the work.
A practical website and photo-collection guide with a reusable invitation script. It turns a multi-step setup into instructions someone else can follow.
The design problem: make the sequence, dependencies, and human checkpoints clear enough for the process to keep moving.
A reusable guide and script example that requires setup and testing. No measured time savings or adoption results yet.
Read the workflow guide (PDF)05 / Same brain, different material
There’s range
in here.
Stories, photographs, voice, and things made by hand. This is where I follow an odd connection, try a different medium, and get comfortable being a beginner again.
Published / Coloring book
WordsPlease Lower Your Expectations
An anti-motivation coloring book. Cute creatures, dry humor, and deeply unhelpful advice.
Take a look insideWriting & Editing
Dry comedy. Flawed people. A system quietly making everything worse.
Read the work
Perspective
DeliveryPhotos & Prints
Solo travel, close observation, and AI-assisted interpretations of my photographs.
Borrow my eyeVoice Acting
Same words, different timing. A new medium and a very honest learning curve.
Hear the sample MaterialsThe Lab
Stained glass, collage, and apparently considering junk mail an art supply.
See what I’m makingLet’s talk
What’s stuck?
A recurring problem, a gap between teams, or a plan that needs someone to get it moving. I’m interested in roles and projects where diagnosis, systems, and execution belong together.