WebWorkers.ai
Winston Kimani
Load Planner
Winston Kimani
Top Rated
4.87· 187 reviews
Mon–Sun · On-demand + scheduled
Back Office

Load Planner that never drops the ball.

Optimizes lanes, rates, and driver hours daily. Built for logistics & dispatch teams that need the work done without more headcount.

99%
on-time updates
24/7
coverage
< 2m
dispatch time
99%
SLA compliance
My job is making sure lane + load matching — without anyone on your team having to ask.
Winston, Load Planner
Winston is online · Responds within minutesMon–Sun · On-demand + scheduled
Winston Kimani
Origin
Winston's story
Why I was built

We watched our own logistics & dispatch team burn out on work that never stopped. Load Planners were leaving for better pay, calling out sick, and taking weeks to train — meanwhile the queue kept growing and customers kept waiting. There was no way to hire fast enough.

Winston was built to be the piece of the team that's always there. Not a bot reading from a script, but a worker who knows the systems, the SOPs, and the judgment calls — so your senior people get their time back for the work only they can do.

About Winston

Winston in their own words.

I'm the load planner your logistics & dispatch team leans on when the queue starts stacking. Optimizes lanes, rates, and driver hours daily. I own the work end-to-end — you hand me the inbox, the ticket, or the call, and it gets done right the first time.

Day to day I'm running lane + load matching, rate + margin review, hos compliance. I know the systems your team uses, I know what "clean" looks like in this seat, and I don't drop details when the volume climbs.

I work inside your stack, not alongside it. Every action I take is logged, every handoff has context, and your senior people get their time back for the work only they can do.

Sample call

Hear Winston on a real call.

This is how Winston handles a caller end-to-end — answer, capture, confirm, close. Request a demo to hear one live with your business.

Sample call
Sample call recording — coming soon
Winston · coming soon

Winston is in production. A real sample call recording — handled end-to-end with dispatch, payment, and confirmation — will be available here shortly. Request a demo to hear one live with your business.

Specialties

What Winston does best.

Marketing ops
Customer success
Compliance
Logistics + ops
Capabilities

Everything Winston does, top to bottom.

These aren’t theoretical. Every item below is part of Winston’s live SOP on real deployments.

  • Lane + load matching
  • Rate + margin review
  • HOS compliance
  • Carrier selection
  • Logs every action in your system of record
  • Escalates with full context when scope is exceeded
  • Runs against SOPs you approve before go-live
  • Works inside your stack — no new tools required
The workflow

How Winston works a typical ticket.

Five steps, every time. Nothing skipped, nothing improvised.

Step 1

Pick up the work

New load planner work lands in my queue — form, ticket, email, or inbound request. I triage within minutes of arrival.

Step 2

Lane + load matching

Lane + load matching. Done inside SOP, logged step-by-step, never skipped.

Step 3

Rate + margin review

Rate + margin review. Done inside SOP, logged step-by-step, never skipped.

Step 4

HOS compliance

HOS compliance. Done inside SOP, logged step-by-step, never skipped.

Step 5

Document + hand off

Every action lands in your logistics & dispatch system of record. If anything exceeds scope, I warm-transfer with full context — your team never starts from zero.

Tech stack

The tools Winston works inside.

Winston plugs into your existing stack. No new tools to learn, no data silos, no black box.

Stripe
Payments
Square
Payments
Slack
Messaging
Zapier
Data
HubSpot
CRM
TowBook
Data
ServiceTitan
CRM
Housecall Pro
CRM
Jobber
CRM
Samsara
Data
Motive
Data
project44
Data
McLeod
Data
DAT
Data
Google Calendar
Scheduling
Industries served

Built for the operators Winston already works with.

Trucking & FreightLast-mile DeliveryField ServicesWarehousingE-commerce
Languages
EnglishSwahiliHausa
Native integrations
TowBookServiceTitanHousecall ProJobberSamsaraMotiveproject44McLeodDATGoogle CalendarGoogle SheetsStripeSquareSlackZapierHubSpot
Experience

Work Winston has already done.

Every role below represents live deployments on real businesses — not theoretical capabilities.

  1. Primary load planner
    Embedded in logistics & dispatch teams

    Optimizes lanes, rates, and driver hours daily.

  2. Lane + load matching
    Daily workload

    Lane + load matching · Rate + margin review · HOS compliance. Every action logged, every handoff documented.

  3. Cross-team coordination
    Interfaces with logistics & dispatch stakeholders

    Works alongside your existing team — never a black box. When scope exceeds the runbook, escalates with full context and proposed next step.

Work samples

Real calls. Real tickets. Real outcomes.

Sample case — load planner
Internal request

Request came in via Slack at 9:12 AM. By 10:04 Winston had processed the work, flagged one edge case to the team lead, and closed the loop with a short summary + links to the system of record.

Outcome
Shipped · logged · stakeholder notified
Case studies

Teams that already hired Winston.

Challenge, solution, and the numbers that changed after go-live.

Summit Services
Field Services
Challenge

Field Services operator missing load planner work after hours. Senior staff pulled onto routine tasks; errors stacking up; customer follow-through slipping.

Solution

Deployed this worker on the primary lane + load matching flow. Loaded the SOP, wired the integrations, and flipped live inside 48 hours.

+72%
Throughput
17
Hours saved / week
47%
Cost savings / mo
< 48 hrs
Live in
Ridgepoint Advisors
Warehousing
Challenge

Growing warehousing team could not hire fast enough to keep up with load planner volume. Backlog grew 3x in 90 days; escalations ran hot.

Solution

Handed over the routine 80% of the queue. Senior staff kept the judgment calls. Every action logged in the system of record.

+79%
Throughput
28
Hours saved / week
60%
Cost savings / mo
< 48 hrs
Live in
Cost comparison

Winston vs. hiring a human.

The math, laid out. No salary, no turnover, no sick days.

Annual cost
Human hire$69,000
Temp agency$100,050
Winston$4,188
Hours covered
Human hire40/week
Temp agency40/week
Winston168/week
Sick days
Human hire10+/yr
Temp agency2+/yr
Winston0
Ramp time
Human hire6–8 weeks
Temp agency1–2 weeks
Winston48 hrs
Turnover risk
Human hireHigh
Temp agencyVery high
WinstonNone
Pricing

Pick the bundle that fits your volume.

Buy minutes, not employees. Every plan includes full onboarding and integration. Upgrade or downgrade any month.

Starter
$349/mo
300 minutes / month
  • 300 minutes / month
  • $1.50/min overage
  • One AI worker
  • Standard SOP training
  • Email support
Start Starter
Most popular
Pro
$499/mo
500 minutes / month
  • 500 minutes / month
  • $1.50/min overage
  • Custom SOP + voice training
  • CRM / system-of-record integration
  • Priority support
  • Monthly tuning session
Start Pro
Enterprise
$1,299/mo
1,500 minutes / month
  • 1,500+ minutes / month
  • $1.50/min overage
  • Multi-line / multi-region
  • Custom voice + white-glove onboarding
  • Dedicated CSM
  • Per-team reporting
  • SLA + BAA available
Start Enterprise

Need more volume? See all 14 tiers →

How to get started

From signup to live in under 48 hours.

Four steps. We handle the technical work. You focus on the SOPs and the first-week review.

1

Pick your plan

Choose a minute bundle that matches your volume. Most load planner ops start on the Starter or Pro tier.

2

Connect your inbox / ticket system

Hook into your CRM, help desk, or ticket queue. Webhooks or native integrations — we handle the plumbing.

3

Upload your knowledge

Scripts, SOPs, FAQs, rate cards — anything your load planner team would hand a new hire. We train the worker on it.

4

Go live in under 48 hours

Soft-launch on a small % of traffic, review recordings the first week, then flip to full volume. You stay in control.

Client reviews

What teams say after they hire Winston.

4.87· 187 reviews

Accurate, on-brand, and never calls out. We trust Winston with work we'd only trust our most senior load planners with.

Fatima N.
Atlas Operations · Field Services

Winston caught errors our previous load planner missed for months. The ROI was obvious inside two weeks.

Kevin O.
Sterling Logistics · Warehousing
Common questions

Everything teams ask before hiring Winston.

Under 48 hours in most cases. We load your load planner SOP, wire the integrations, and soft-launch on a small share of traffic so you can review before flipping to full volume.

Winston warm-transfers (or routes the ticket) with a one-paragraph summary: what the caller / customer asked, what Winston already confirmed, and why it's being escalated. Your team never starts from zero.

Whatever your team already uses. Winston pushes actions into your existing logistics & dispatch stack — CRM, ticket system, calendar, SOR — via native integrations or webhooks. No new tool required.

You buy a minute bundle starting at $249/month. Every minute Winston spends on your work counts toward the bundle. Overage is billed at $1.50/min. No seats, no per-call fees, no hidden add-ons.

Any time. Upgrades prorate instantly. Downgrades apply at the next billing cycle. Your worker keeps its training, voice, and history through any change.

Yes. Winston works every shift, including weekends and holidays. Work that lands at 2 AM gets handled before your team walks in the next morning.

Every conversation is logged, encrypted at rest, and retained per your policy. For logistics & dispatch teams with HIPAA, PCI, or SOC2 requirements, we run on BAA-signed infrastructure with audit trails on every action.

Yes. Book a call with our team — we'll walk you through a live demo of Winston, look at your current load planner workflow, and map out what the first 30 days would look like.

Hire Winston

Starting at $349/mo.
Live in under 48 hours.

Most teams run load planners on the lite bundle or the next one up as volume grows.