Senior Implementation Manager Chicago, IL

FrontApp Inc.; Chicago, Northern (IL, KY); Hybrid; USD 120,000 - 180,000; Full time

Benefits offered by this job

Health insurance

Parental leave

Flexible time off

Work-from-home days (Mon & Fri)

Job summary

Front seeks a Senior Technical Project Manager / Senior Implementation Manager to lead its most complex customer implementations—from onboarding to value realization. You will partner with customer leaders, translate workflows into scalable Front configurations, and drive governance, risk, and adoption across multi‑workstream programs.

This hands-on leadership role requires independent management of high‑stakes engagements, while improving playbooks, reusable solutions, and cross‑functional

Qualifications

• 5+ years leading customer-facing SaaS implementations or complex transformation programs.
• Own complex implementations from discovery through sustained adoption with multiple stakeholders.
• Diagnose underlying business problems and recommend practical future state beyond requirements.
• Demonstrate strong project leadership: scope, timelines, governance, risk, and exec communication.

Responsibilities

• Own multi-workstream implementations from discovery through launch and adoption.
• Advise on future-state workflows, operating models, governance, and change management.
• Build clear project plans, risk registers, and executive updates across engagements.
• Lead discovery workshops to uncover goals, gaps, constraints, risks, and success criteria.
• Drive solution design with integrations, data flows, migrations, and APIs; engage specialists as needed.
• Lead change management, enablement, cutover, and adoption strategies for transitioning from legacy tools.
• Navigate escalations and align customer and internal teams on a path forward.
• Partner with Sales, Solutions, Product, Engineering, and Support to define scope and unblock blockers.

Skills

SaaS Implementations

Project Leadership

Change Management

Systems Thinking

Technical Fluency

Executive Communication

Job description

Front is the customer operations platform built for B2B complexity, keeping every team, tool, and customer conversation in sync so companies can scale without losing connection. Others handle simple interactions. Front handles the coordination and context behind complex B2B customer relationships. Over 9,000 companies, including Uber Freight, Navan, and Stripe, rely on Front because it's the only one that can run the operational layer that makes customer-facing work actually succeed.

Backed by Sequoia Capital and Salesforce Ventures, Front has raised $204M from leading venture capital firms and independent investors including top executives at Atlassian, Okta, Qualtrics, Zoom, and PagerDuty. Front has received numerous Great Place to Work accolades, including Top Places to Work by USA Today 2025, Y Combinator's list of Top Companies in 2023, #4 on Fortune’s Best Workplaces in the Bay Area™, Inc. Magazine's 2022 Best Workplaces list, and Forbes Best Startup Employers 2022 List.

We’re looking for a Senior Technical Project Manager / Senior Implementation Manager to join our Success Services team in the US. You will lead Front’s most complex customer implementations across net-new onboarding, enterprise expansion, workflow transformation, migration, and adoption of new capabilities.

You will be the customer’s primary implementation partner and a senior advisor throughout the engagement. You’ll uncover business goals, translate complex processes into scalable Front workflows, establish the project operating model, lead change and enablement, navigate technical dependencies, and drive teams toward measurable value.

This is a hands‑on role for an experienced implementation leader. You will independently manage high‑stakes engagements while also improving how our team works through stronger playbooks, reusable solutions, coaching, and cross‑functional partnership.

What will you be doing?

• Own complex, multi-workstream implementation engagements from discovery and solution design through launch, adoption, and value realization.
• Advise customer leaders on future‑state workflows, operating models, governance, and change—not simply configure stated requirements.
• Build and drive clear project plans, decision frameworks, stakeholder cadences, risk registers, and executive updates across multiple concurrent engagements.
• Lead discovery workshops that uncover business goals, process gaps, technical constraints, change risks, and measurable success criteria.
• Guide solution design involving permissions, integrations, data flows, automations, migrations, APIs, webhooks, and Front’s AI‑powered capabilities; independently handle common technical topics and engage specialists intentionally.
• Lead change management, enablement, cutover, and adoption strategies for teams moving from deeply embedded legacy tools and processes.
• Navig local escalations with calm judgment, clear ownership, and an ability to align customers and internal teams around trade‑offs and a path forward.
• Partner with Sales, Solutions, Account Management, Product, Engineering, and Support to define scope, resolve blockers, and improve the customer journey.
• Turn recurring customer needs into reusable implementation assets, playbooks, templates, and delivery improvements.
• Support team development through mentoring, thoughtful feedback, knowledge sharing, and leadership on strategic initiatives.
• Represent the customer voice and implementation perspective in product and operational decisions.

What skills & experience do you need?

• 5+ years of experience leading customer‑facing SaaS implementations, professional services engagements, technical programs, or similarly complex transformation work.
• A track record of independently owning complex implementations from discovery through sustained adoption, including multiple stakeholders, workstreams, and technical dependencies.
• Strong consultative and systems‑thinking skills; able to diagnose underlying business problems and recommend a practical future state rather than order‑take.
• Excellent project leadership, including scope, timeline, governance, risk, executive communication, and management of multiple concurrent priorities.
• Demonstrated change‑management experience, including stakeholder mapping, resistance management, enablement, cutover, and reinforcement after launch.
• Strong technical fluency across integrations, permissions, data flows, automations, migrations, APIs, and webhooks; able to learn products quickly and know when deeper expertise is needed.
• Executive presence and communication skills, with the ability to simplify complexity, facilitate difficult decisions, and build trust across technical and non‑technical audiences.
• Sound judgment under pressure and experience recovering at‑risk projects or resolving escalations.
• Evidence of improving a services organization through reusable solutions, delivery methodology, enablement, mentoring, or operational improvements.
• Curiosity and practical judgment about AI and automation, including how to drive responsible customer adoption and improve personal effectiveness.

What makes you a great fit?

• You create clarity and momentum when the path is ambiguous.
• You challenge assumptions respectfully and make recommendations grounded in customer outcomes.
• You connect business strategy, workflow design, technical constraints, and change management.
• You communicate credibly with executives while staying close to execution details.
• You anticipate risks early, make trade‑offs explicit, and recover quickly when plans change.
• You measure success by adoption and value—not activity or go‑live alone.
• You improve the system around you and help teammates raise their craft.

Front operates on a hybrid model — we come together in the office each Tuesday, Wednesday, and Thursday to collaborate and stay connected.

What we offer

• Competitive salary
• Equity (we are post-series D & backed by some of the best VCs in the US)
• Private health insurance, including plan options at no cost to employees
• Paid parental leave
• Flexible time off policy
• Flexibility to work from home Monday and Friday, unless posted as a fully remote role
• Mental health support with Workplace Options
• Family planning support with Maven
• $100 per month Lifestyle Stipend to spend on fitness, health and wellness, and other activities
• Wellness Days - Fronteers get an additional day off on months with no holidays
• Winter Break - Our offices are closed from Christmas to New Year's Day!

Front provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age or disability. By applying, you acknowledge and agree that you have read and understand the California Recruiting Privacy Notice & EU Privacy Notice