Senior Product Manager

Ships the version people actually use

Eight years turning messy operations problems into products dispatchers, drivers and finance teams open every morning. I plan against a number, ship in small cuts, and write down what I got wrong.

Role Senior Product Manager
Years 8 in B2B software
Location Toronto · hybrid or remote
Available January 2027
Portrait
Rachel Bennett Leslieville, Toronto
Open to work Group PM and Director of Product roles, Series B to D, from January 2027. Eight weeks' notice.

Employers

Three companies, one thread

Every role was in software that moves parcels or money for small operators. The thread is the same: make the tool the team opens first.

Parcelo Now Senior Product Manager Shipping platform for mid-market carriers, Series C 2023 - now
Ledgerline Product Manager Invoicing and reconciliation for small firms, Series B 2020 - 2023
Cartage Support analyst, then Associate PM Freight marketplace, seed to Series A 2018 - 2020

About

The short version

Who I am when the roadmap review is over.

I started on the support desk at a freight startup, answering the same eleven questions about where a truck was. Rewriting the tracking page so nobody had to ask them was my first product, and the pattern has not changed since: sit with the people who use the thing, find the ten minutes that ruin their day, and take it out.

Eight years later I run dispatch and payouts at Parcelo, a shipping platform for mid-market carriers. My teams ship in small cuts, plan against a written target, and read the number back when the quarter closes. The launches on this page are the ones that moved it.

I am looking for a Group PM or Director role where the product is operationally hard and the team is small enough that the decision log still fits on one wall.

Portrait
How I work

One page per decision: the options, the number we expect, who disagreed. Reviewed every quarter, the wrong calls marked in red.

Off the clock

A folding bike, a sourdough starter that has outlived two apartments, and Saturday mornings at the St. Lawrence Market.

What people remember

I ask "what would we have to see to stop this?" before we start, and I write the answer down.

214 decisions in the log since 2020. Forty-one marked wrong, all of them cheaper than the ones we did not write down.

Experience

Where the work happened

Four roles at three companies, each with the thing it added. The full CV is one click away.

2023 - now Now Senior Product Manager Parcelo · Toronto, ON

Own dispatch and payouts for a shipping platform used by 140 mid-market carriers; five engineers, one designer, one analyst. Shipped the Dispatch Board (38% less time to dispatch a day, median across 41 carriers), Instant Payouts (92% driver opt-in in six months on a new payments rail) and Rate Cards v2 (+21% self-serve signups). Hired and coach two product managers.

2020 - 2023 Product Manager Ledgerline · Toronto, ON (hybrid)

First PM for the accounting side of an invoicing product for small trades firms. Took Reconcile from a customer's spreadsheet macro to the reason the middle plan exists (about 6,000 bookkeeper hours a year given back), and cut time to first invoice from nine days to one (thirty-day activation 41% to 63%).

2019 - 2020 Associate Product Manager Cartage · Toronto, ON

Owned the shipper-facing tracking and notifications area of a freight marketplace after writing its first product from the support queue. Ran the beta program and the weekly release note.

2018 - 2019 Support Analyst Cartage · Toronto, ON

First job in software: answered the same eleven questions about where a truck was, then specified the tracking page that made them stop. "Where is my order" tickets fell 54% in its first quarter.

Read the full CV Download the PDF

By the numbers

What the work moved

Each figure is the one that was reported when the quarter closed, with where it came from.

38% less time to dispatch a day's routes Median across 41 carrier accounts, twelve weeks after the Dispatch Board launch, measured against the same weeks a year earlier.
92% of drivers opted into same-day pay Instant Payouts, six months after launch
6,000 hours a year given back to bookkeepers Ledgerline Reconcile, summed across customers
9 → 1 days from signup to first invoice Onboarding in a day, median new account
54% fewer "where is my order" tickets Cartage Tracking, first quarter live
4 product teams built and handed over Two still shipping on the original roadmap
214 decisions in the log Forty-one marked wrong, reviewed quarterly

Projects

Six things I shipped

Each one with the company, the year, my part in it and the number it moved. Open any of them for the whole story.

Skills

What I bring to a team

Grouped the way the work actually splits, with how deep each group goes.

Discovery Core Finding the ten minutes that ruin a dispatcher's shift.
  • Ride-alongs and shadowing
  • Customer interviews
  • Jobs to be done
  • Opportunity trees
  • Support ticket mining
Delivery Core Shipping in small cuts against a written target.
  • PRDs and one-pagers
  • Roadmaps
  • Release planning
  • Feature flags
  • Beta programs
  • Post-launch reviews
Data Strong Enough SQL to check the number myself.
  • SQL
  • Metabase
  • Amplitude
  • Experiment design
  • Cohort analysis
  • Spreadsheets that scale badly
Leadership Strong Teams that keep shipping after the handover.
  • Hiring PMs
  • Coaching
  • Stakeholder plans
  • Quarterly planning
  • Board updates
  • Decision logs

How I work

The first ninety days, every time

The same four moves whether the product is dispatch, payouts or a page nobody has opened yet.

Sit with the people who use it

Two weeks of ride-alongs, support shifts and screen shares before I open a roadmap. I am looking for the ten minutes that ruin a day, not a feature request.

You get A one-page problem brief with the number we expect to move
Write the target before the work

Every initiative gets a written target, the options we passed on and who disagreed. It goes in the decision log and it is read back when the quarter closes.

You get A decision-log entry and a quarterly target the team signed
Ship in small cuts

Feature flags, a beta of ten accounts, then the rest. Nothing waits for the big launch, and the first cut is usually embarrassing on purpose.

You get A beta in four weeks and a release note the support team can read
Read the number back

Twelve weeks after launch we measure against the target, mark the call right or wrong in the log, and decide what to stop. Stopping is a deliverable too.

You get A post-launch review, with the wrong calls in red

References

What the people I worked with say

A manager, a report, a peer and a customer. Contact details for all four on request.

Rachel is the PM I hand the hardest operational problem to. She came back from two weeks of ride-alongs with a one-page brief, a number, and a plan that shipped a beta in a month. Twelve weeks later the number was on the board and she was the one who marked which of her own calls had been wrong.
Daniel Okafor VP Product, Parcelo Manager
She taught me to write the target before the work. I still use her one-pager template, and I still hear her asking what we would have to see to stop.
Priya Nair Product Manager, Parcelo Report
Engineering trusted her because the scope never moved after the kickoff, and when it had to, she was the one who said so first, in writing.
Marcus Lindqvist Engineering Manager, Ledgerline Peer
We run forty vans. The dispatch board gave my morning back. She sat in our office for three days before she changed a single screen.
Rosa Delgado Operations Director, Northline Courier Customer

Looking for

The next role, specifically

Written down so we can both tell in a minute whether it is a fit.

I want to run a product area that is operationally hard - dispatch, payments, scheduling, the unglamorous middle of a business - with a small team of PMs who will write their targets down and let me read them back.

Role Group PM or Director of Product Two to four PMs reporting in, one product area owned end to end
Company Series B to D, B2B software Fifty to five hundred people; operations, logistics or fintech preferred
Where Toronto hybrid, or remote across North America In the office two days a week is ideal; quarterly travel is fine
When From January 2027 Eight weeks' notice; a proper handover of dispatch and payouts
How A team that writes its targets down And reads them back when the quarter closes
Not for me
  • Agency or consultancy work
  • A solo PM before product-market fit
  • Fully on-site outside Toronto
  • A roadmap already written for the year

Practical

The questions recruiters ask first

Answered here so the first call can be about the role.

What is your notice period?
Eight weeks. I would rather hand dispatch and payouts over properly than start a week earlier, and the team deserves a clean transition.
Remote, hybrid or in the office?
Hybrid in Toronto is ideal - two days a week in a room with the team. Fully remote across North American time zones works too, with quarterly travel.
Would you relocate?
Not for this move. Toronto is home, and the roles I want are here or remote. I am happy to travel to a head office regularly.
Do you need visa sponsorship?
No. I am a Canadian citizen, and I can work for a US company remotely under a standard contractor or employer-of-record arrangement.
What are you expecting on compensation?
In line with a Director of Product at a Series B to D company in Canada or the US. I would rather talk about the range early than late.
Can I speak to references?
Yes - a manager, a report, a peer and a customer, all quoted on this page. I will make introductions after a first conversation.

The whole record, two pages.

Every role, every launch and the number each one moved, in the order a hiring manager reads them. The same facts as this page, without the scrolling.

Download the CV PDF · 2 pages · updated September 2026

Contact

Tell me about the role

The team, the product area and the number it has to move. I reply to everything.

Your name
Work email
The role, the team and the number
Email [email protected] The fastest route. The form works too.
Where Toronto, ET Hybrid, or remote across North America
Replies Within a day Usually the same afternoon
Elsewhere