Peter Lebedev
Peter Lebedev
Greater Boston, MA · LinkedIn · Email

Twenty-five years building software.
From IC to director and back again.

I have spent my career building systems, leading engineering teams, and navigating the space between the two. I stay close enough to the work to understand where things break — and that is a deliberate choice.

Philosophy

The leader should understand the problem

If a technical leader cannot sit with the team and work through the difficult problem together, then that person is not truly leading the technical effort. They are managing around it. Sooner or later, the product reflects this.

This is not an abstract belief. It is the result of watching — over two decades — what happens when technical leadership disconnects from the work. The decisions get slower. The architecture drifts. The team notices. I moved from individual contributor to senior director and then chose to move back. That was deliberate.

Career arc

The path — not a straight line

Scroll through 25+ years from Moscow State University to building GenAI systems in Boston. The milestones that shaped the trajectory are marked.

1993 – 1998
M.S., Mechanics & Mathematics
Lomonosov Moscow State University
Where it started. Mathematics and mechanics — the kind of foundation that shapes how you think about systems long before you write any code.
Education
1998 – 1999
Software Engineer
Renova · COPF
Early career roles in software engineering. The beginning.
IC
2000
Software Engineer — First US Role
PTC
Joined the Manufacturing team — my first role in the United States. Developed NC machining algorithms while adapting to new technologies and engineering practices. This is where a decade-long journey at PTC began.
IC
2001 – 2006
Senior SE → Principal SE → Senior Technical Consultant
PTC
Progressed from independent work on complex NC algorithms to broader cross-team scope on the Pro/Engineer–Windchill PLM integration, with increasing involvement in design and architecture decisions.
IC
2008 – 2010
Software Development Manager
PTC
First management role. Led a team of 4 engineers on core integration components. Also drove the effort to extend Windchill to support third-party CAD tools.
Leadership
2010 – 2014
Software Architect & Team Lead
KAYAK
Owned the full backend design of KAYAK's native booking product. Built the first integrations for flights, hotels, and cars myself — on purpose — to find the real patterns before encoding them into a framework others could extend.
IC + Architecture
2015
Principal Engineer
Jobcase
Joined as part of a small platform team. Focused on scalable backend services, data pipelines, and establishing code quality practices that would scale with the company.
IC
2016 – 2019
Software Engineering Manager
Jobcase
Led a small team on foundational backend systems — session management, user data, compliance, communication infrastructure. Not the most visible work, but the kind everything else depends on.
Leadership
2019 – 2021
Director of Engineering — Job Search Platform
Jobcase
Led up to 15 people. Migrated the search engine from Elasticsearch 2.x to 7.x. Created and ran the monthly Product & Engineering session for 5+ years. Highest engagement scores in the company.
Leadership · Peak team size
April 2021
Jobcase Acquires Upward.com
Jobcase + Upward
The acquisition that changed the next chapter. Two search engines, two engineering teams, one private data center that needed migrating to AWS.
Acquisition
2021 – 2023
Senior Director — Search Platform Integration
Jobcase
Led the post-acquisition integration. Re-platformed Upward services to AWS, merged the engineering teams, built out A/B testing and configurable search strategies.
Leadership
2024 – Present
Senior Director — GenAI & Engineering Leverage
Jobcase
Back to building. Effort-leadership, not people-management. Building the core routing framework and production AI systems — phone, SMS, direct messaging — handling over 1.4M leads since launch.
IC-scope leadership

Growing with the company

I joined Jobcase in 2015 when it was a small company. Over the next several years, the organization grew from under 100 to over 300 people. My roles evolved with it — from principal engineer to director to senior director, and then deliberately back toward hands-on technical work.

~2015
< 100 people
Principal Engineer
~2019
~150 people
Director of Eng
~2021
~250 (+ Upward acquisition)
Sr. Director — Integration
~2022+
300+ people
Sr. Director — GenAI
GenAI Systems

What I built — and at what scale

The current role is about getting GenAI into production in ways that actually work. Not demos. Not experiments. Production systems handling real volume across multiple channels.

Phone 1.25M leads SMS 225K leads Direct Msg Routing Framework Java Microservices Core orchestration layer Agent Lambda A Python Agent Lambda B Python Agent Lambda N Python Other teams extend agents without touching the core CS Automation: ~40 hours/month of manual work eliminated
0
Phone leads handled
since Q2 2025
0
Unique SMS leads
since Oct 2025
3
Channels live
Phone · SMS · DM
40h
Monthly manual work
eliminated for CS team

Product & Engineering Monthly

I created and ran this session for over five years, through the company's growth from under 100 to over 300 people. Three presenters each month. One hour. Speakers came from across the entire company — not just product or engineering.

Every presentation followed the same framework. Click each step to see what it means.

01
What
What problem are you working on? Not the project name, not the Jira epic — the actual problem. What is broken, missing, or not good enough?
02
Why
Why does this matter for the business? Not "my manager asked me to" — the real reason. Revenue, retention, reliability, user experience. Connect the work to the outcome.
03
How
How are you solving it? The technical approach, the tradeoffs, the things you tried that didn't work. This is where the room learns the most.

The format was simple on purpose. It forced clarity — if you cannot explain What, Why, and How in twenty minutes, you probably do not understand the problem well enough yet.

Search platform

Elasticsearch Migration — Before & After

Migrated the core job search engine from Elasticsearch 2.x through 6.5 to 7.x. The numbers tell the story.

Before (ES 2.x)

Error rate baseline
Latency baseline
Weekly
Incidents needing attention

After (ES 7.x)

20×
Error rate reduction
Latency improvement
Rare
Incidents needing attention

A place where this matters

Looking for a senior technical leadership position where the leader is expected to understand the problem as deeply as the engineers solving it. People leadership with hands on the keyboard, or senior IC with cross-team scope. Either way, close to the work.