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Online tutoringOne-on-one math support

Case study · Online tutoring

How a tutoring founder
got her remote team
up to speed fast

Two Unicorns, hired weeks apart, took finance and the founder's calendar off her plate. She is hiring a third.

Kyle
Kyle
Janesha
Janesha
  • 2Unicorns placed
    weeks apart
  • 3weeks to become
    the founder's filter
  • 30days from daily
    to weekly check-ins
  • 3rdUnicorn now
    being hired
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Client
Katie WalkerCEO and founder, online tutoring
Business
One-on-one mathFor students with learning differences
Unicorns
Kyle and JaneshaFinance Ops and Executive Assistant
Outcome
Two roles running on their ownA third Unicorn being hired

The story in ten slides

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  1. When all three sides show up, new hires stop feeling new fast: how a tutoring founder brought two Unicorns into her business and had both fully integrated within weeks
  2. The problem: one founder carrying the whole back office, with the books behind, multi-state payroll gaps, and a slipping inbox and calendar
  3. The match: two Unicorns, two jobs off her plate, a finance and bookkeeping Unicorn who already knew QuickBooks and Stripe, and an Executive Assistant for the inbox, the calendar and the team
  4. Why this worked: a successful hire has three parts, the right talent, Assistantly's support, and the client
  5. The Unicorns: both went past the brief in their first weeks, writing SOPs, catching a payroll discrepancy, and lining up every open decision before each check-in
  6. The client: she explained the why behind every task, with weekly check-ins, a shared tracker, SOPs and Loom walkthroughs from day one
  7. By the numbers: 2 Unicorns placed close together, 3 weeks to become the founder's filter, 1 Unicorn now being hired
  8. The ramp: daily finance check-ins scaled back by week 2, the EA became the founder's filter by week 3, check-ins moved to weekly by day 30, and payroll now runs independently
  9. Client perspective: “She came with so much experience and expertise. Hiring Kyle has gone fantastically.” Katie Walker, CEO and founder
  10. What comes next: her first two Unicorns are now onboarding the third

Or read the full story ↓

The storyTwo hires, weeks apart

Katie Walker's specialized online tutoring business, one-on-one math support for students with learning differences, was growing fast, and she couldn't keep handling admin and finance on her own anymore.

She brought on two Unicorns close together: one for finance and bookkeeping, one as her Executive Assistant. Both were fully integrated into the business within weeks. The partnerships have worked so well that she's now hiring a third.

This is what made it work, on all three sides: the client, the Unicorns, and Assistantly.

Where pressure was building

As the business grew, the founder was carrying more than one person could manage.

  • Books were significantly behind and prior year taxes weren't cleared
  • Multi-state payroll compliance had gaps she couldn't fully scope
  • Existing finance SOPs were generic and inconsistent
  • Her inbox and calendar were starting to feel unmanageable

Every new hire also meant time spent training them.

That time was the one thing she had least of.

On the Assistantly side

What Assistantly put in place

Assistantly found the right people and kept the feedback loop tight. The client and the Unicorns did the rest.

01

Finding the right people

Assistantly placed talent who could ramp up quickly. The finance Unicorn already knew QuickBooks, Stripe, and banking software, so she could focus on learning the business instead of the tools. Ramp time was still needed, just less of it.

02

Structured onboarding and integration

An onboarding call for each Unicorn, with Client Experience and Talent both present, documenting tools, training plan, communication rhythm, and what success looks like.

03

Success plans

Each Unicorn received a success plan based on the way the client operated and the outcomes she needed.

04

Support after day one

Check-ins on expectations in the first week, then at 2 weeks, 30 days, and 60 days.

On the client side

What the founder brought

  • Treated the Unicorns as employees and team members, not task-doers
  • Explained the why behind every task, not just the what
  • Set up structure from day one: weekly check-ins, a shared task tracker, SOPs, and Loom walkthroughs
  • Let the Unicorns shape the process instead of dictating it
  • Protected time for training, even when her calendar was stretched
  • Shared even the smallest feedback early, because small friction left alone turns into bigger friction

On the Unicorn side

Both went past the job description

Both Unicorns went beyond what was expected in their first weeks, which made onboarding easier on everyone.

Kyle

Finance and bookkeeping

  • Wrote SOPs from scratch for undocumented tasks she knew she'd repeat, and had the founder review them
  • Checked payroll on her own, caught a discrepancy, and resolved it before the founder had to follow up
  • Met with the outgoing team member on her own to absorb as much context as possible
  • Used Claude to research questions first, then brought what she couldn't solve to the founder

Janesha

Executive Assistant

  • Proposed daily 15 to 20 minute check-ins
  • Offered to work with the founder to reorganize outdated documents
  • Reached out to other team members on her own to learn the business
  • Lined up anything that needed the founder's input before each check-in, so nothing got blocked

What changed

Overseeing less,
delegating more

  1. Kyle

    Finance and bookkeeping

    • Daily check-ins were scaled back by week two, and moved to weekly by day 30
    • The founder no longer oversees core bookkeeping day to day
    • Payroll runs independently, and compliance moved into a managed payroll tier with vendor support
  2. Janesha

    Executive assistant

    • Became the filter between the founder and her team within three weeks
    • Planned the third hire's first week of training, set up their access, and helped lead their onboarding
    • The founder took her first real time off, two days, in the middle of a staff transition
  3. The partnership

    Work that used to sit on her plate

    • The founder now trusts both Unicorns with it
    • The first two Unicorns are now helping bring the next hire up to speed
3rd
Unicorn now being hired

The founder went from carrying finance, scheduling, and team coordination herself to leading a team that handles them. Because it's working, she's hiring again.

★★★★★
“She came with so much experience and expertise! Hiring Kyle has gone fantastically.”
★★★★★
“She jumped in to solve 2 problems before I even anticipated she would be ready to do them independently. Very happy so far.”

Katie WalkerCEO and founder

Why this worked

A successful hire has three parts

Great talent is only one of them.

The first third: the right talent

Assistantly finds people who can ramp up quickly and take ownership early. That's where most placement agencies miss the mark in shaping soft skill matches.

The second third: Assistantly's support

Every partnership gets structured onboarding and integration, success plans, and ongoing HR and payroll support.

The last third: the client

This founder gave her Unicorns context, structure, and room to shape how the work got done, and she raised feedback early instead of letting it build.

When all three show up,
new hires stop feeling new fast.

Tell us the first
role to hand off

We'll find someone who can take it over, and stay with the partnership long after day one.

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