Lead Implementation Specialist, T&S

About UsPerk (formerly TravelPerk) is the intelligent platform for travel and spend management. Built to tackle the time-consuming, manual work that gets in the way of real work, our tools automate everything from travel bookings to expenses, invoice processing, and more. By eliminating this shadow work that wastes hours, erodes morale, and saps innovation, we’re on a mission to power real work, with real impact.We’re trusted by more than 10,000 companies worldwide, including Wise, On Running, Breitling, and Fabletics, and we’re tackling the 7 hours of lost productivity per employee each week, a $1.7 trillion problem.Founded in 2015, Perk has grown into a global company of more than 1,800 people across 12 offices globally, with headquarters in London and Boston. We combine innovation, control, and simplicity to transform how businesses work and how people feel at work.At Perk, we’re driven by our values, like being an owner, delivering a 7-star experience, and working as one team. We value curiosity, purpose, and mindset, not just knowledge, to unlock the power in your potential. Our talent team brings together leading minds from the travel and SaaS industries, representing over 70 countries. If you’re excited about having a real impact and shaping how millions of people experience work, we’d love you on the team.Visit to learn more.The RoleAs 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-classWhat you’ll doOwn 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-solvingApply 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 bring3–4+ 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 experienceStrong 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 attitudeBonus 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 implementationExperience in Spend Management solution or ERP implementationEnglish 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 base salary is $110,000, and the OTE is $134,000 (base + commission), plus equity. The commission structure will be tied to achieving revenue & 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 WorkAt 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.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.Protect Yourself from Recruitment ScamsAll official communication from Perk will always come from email addresses ending in @perk.com or @externalperk.com, our verified social media channels, or recruiters listed on our official LinkedIn page. We will never ask you to pay for equipment, training, or fees, request sensitive personal information such as bank details early in the process, or communicate through unofficial apps like WhatsApp, Telegram, or Signal. If you receive a message claiming to be from Perk that seems suspicious, please do not respond. Forward it to security [at] perk .com, and we will confirm whether it is legitimate.#LI-HybridCompensation Range: $134KLocationChicago; BostonAddressChicago, IllinoisEmployment TypeFull timeLocation TypeHybridDepartmentSalesCompensationOTE $134K • Offers Commission