Lead Implementation Specialist, T&S

Traveltechessentialist; Chicago (IL); On-site; USD 115,000 - 145,000; Full time

Job summary

Traveltechessentialist in Chicago is seeking a Lead Implementation Specialist to manage onboarding projects for SMB and Enterprise customers. The role involves coordinating multiple stakeholders and ensuring effective project delivery, especially with ERP systems. Applicants should have 3-4 years of experience in project management, excellent communication skills, and a keen understanding of financial processes.

This position is critical in guiding customers through complex integrations, with a compensation package that includes salary, commissions, and equity, estimated at $129,000 OTE.

Qualifications

• 3-4+ years of experience in customer-facing roles, with at least 2 years in project management.
• Solid technical or financial acumen through education or experience.
• Strong communication skills for stakeholder alignment.

Responsibilities

• Own high-complexity projects with ERP integrations while ensuring successful adoption.
• Coordinate multiple stakeholder groups to keep everyone aligned.
• Design advanced setups, including complex customizations.

Skills

Project management

Customer-facing roles

Communication skills

Problem-solving

Financial expertise

Tools

ERP systems (NetSuite, Dynamics BC, Dynamics F&O)

Job description

The Role

As a Lead Implementation Specialist – Travel & Spend, you’ll own high‑complexity onboarding projects for our SMB and Enterprise customers. You will work with Travel, Expense and Invoice Perk Products, leading projects that often involve ERP integrations. You’ll be the driving force that keeps internal teams, customer stakeholders, and external partners aligned, ensuring smooth rollouts, rapid adoption, and successful go‑lives.

With your deep product knowledge, strong financial acumen, and understanding of ERP systems, you’ll guide customers through sophisticated setups while acting as a trusted advisor. You’ll lead by example, coaching team members and shaping a world‑class

What you’ll do

• Own high‑complexity projects with ERP integrations, ensuring structured delivery and successful adoption across Travel & Spend.
• Coordinate multiple stakeholder groups including finance leaders, project managers, IT teams, and external consultants, keeping everyone aligned and focused on shared goals.
• Design advanced setups, including some complex customizations that require creative thinking and problem‑solving.
• Apply financial expertise to onboard Invoice modules, helping customers adopt policies, workflows, and processes with confidence.
• Understand ERP systems and finance tech (NetSuite, Dynamics BC, Dynamics F&O) – you won’t need to code or troubleshoot, but an interest in these systems, their data flows, and their role in the customer journey is key.
• Coordinate internal and external technical teams to ensure integrations are delivered smoothly.
• Resolve escalations proactively, providing solution‑oriented guidance when challenges arise.
• Mentor and guide more junior Implementation team members, sharing best practices, technical knowledge, and tips for successful onboarding.

What you’ll bring

• 3–4+ years of experience in customer‑facing roles, with at least 2 proven years in project management, ideally within implementation projects.
• Solid technical and/or finance acumen either through education or working experience.
• Strong communication and stakeholder alignment skills – you’ll keep internal teams and customers coordinated toward a common goal: a successful onboarding.
• Highly organized, detail‑oriented, and able to manage multiple moving parts without losing sight of quality.
• A true problem‑solving and team‑player attitude.

Bonus points for…

• Prior experience with self‑serve or custom integrations (SSO, HRIS, SCIM, ERP, CRM) and a strong interest in ERP systems, finance, and the technology around them.
• Experience in consulting, finance, or direct customer onboarding/technical implementation.
• Experience in Spend Management solution or ERP implementation.
• English language working proficiency is a must; other languages are a strong plus.

Compensation

Compensation for this role is a combination of salary, commissions, and stock options. The OTE is $129,000, plus equity. The commission structure will be tied to achieving revenue and retention targets.

AI Fluency

AI is embedded in how we work across every function. The tools you’ll use day‑to‑day are AI‑enabled so you can move faster and spend more time on the work that matters. In practice, that means using AI to research and prioritise accounts, draft and refine outreach, handle customer interactions more effectively, synthesise information, and cut through shadow work – the invisible tasks that pull people away from the work only they can do – so you can focus on relationships and outcomes.

We don’t expect you to be an AI expert, but we do expect you to be curious and intentional about it. The bar is judgment: knowing when AI makes your work better, when to verify what it produces, and when to rely on your own expertise instead.

We’ll ask about how you use AI in your interviews, not to test tool knowledge, but to understand how you think about it. That reflects how we work every day.

How We Work

At Perk, we take an IRL‑first approach to work, where our team works together in‑person 3 days a week. As such, this role requires you to be based within commuting distance of our hubs. We fundamentally believe in the value of meeting in real life to improve connectivity, productivity, creativity and ultimately making us a great place to work.

For certain roles, we can help with relocation from anywhere in the world. English is the official language at the office. Please submit your resume in English if you choose to apply. Do not forget to submit an updated portfolio and/or resume.

Equal Opportunity Employer

Perk is a global company with a diverse customer base, and we want to make sure the people behind our product reflect that. We’re an equal opportunity employer, which means you’re welcome at Perk regardless of how you look, where you’re from, or anything else that makes you, well, you.