Sales Jobs in Illinois (Now Hiring) — 10,490 open — Page 342

About Us

Perk (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 www.perk.com to learn more.

About the role:

Perk is best known for transforming business travel — but our ambitions don't stop there. Following our acquisition of Yokoy, we've built an integrated Spend management platform that's already reshaping how European companies control expenses, manage procurement, and unify financial workflows. Now we're bringing it to the US, and we need the people to lead that charge.

We're building a dedicated Spend team — a group of elite sales professionals who know this space deeply, can navigate complex multi-stakeholder deals, and are ready to help define what Perk Spend means in the North American market. This is a ground-floor opportunity to shape a category, build a book of business from scratch, and grow with the product as it scales.

This is not a travel sales role. Spend is a fundamentally different, more complex sale — touching Finance, Procurement, IT, and the C-suite — and we're looking for people who've lived that complexity before and thrived in it.

How you'll spend your time:

• Own the full sales cycle for Perk Spend — from outbound prospecting and pipeline generation through discovery, multi-stakeholder demos, commercial negotiation, and close.

• Build net-new pipeline through strategic outbound activity across phone, email, LinkedIn, and industry networks, targeting mid-market and enterprise Finance, Procurement, and Operations leaders.

• Run consultative, insight-led discovery to understand the real complexity of a prospect's spend workflows — T&E, AP, procurement, card programs — and map Perk Spend's capabilities to those needs.

• Navigate multi-threaded deals involving CFOs, Controllers, IT, and Procurement, building consensus and managing competing priorities across the buying committee.

• Develop and deliver tailored business cases and ROI narratives that resonate with financial decision-makers, not just end users.

• Partner closely with Solutions Engineering, Implementation, and Customer Success to ensure prospects understand the full platform value and customers land successfully.

• Contribute to our go-to-market playbook as an early Spend hire — sharing market feedback, refining messaging, and helping shape how we position this product in the US.

• Maintain rigorous pipeline hygiene and accurate forecasting in Salesforce, operating with the discipline of someone who takes ownership of their number.

What you’ll bring:

• 3-5+ years of full-cycle B2B sales experience, with a meaningful portion spent selling Spend Management, expense management, AP automation, procurement, ERP, or adjacent fintech / finance tech solutions.

• A genuine hunter mentality — you're energized by building pipeline in a new market, not just managing inbound or an existing book.

• Experience navigating complex, multi-stakeholder enterprise deals where Finance or Procurement is a key buyer or champion.

• The ability to speak credibly to financial workflows: you understand how companies think about spend controls, approval chains, policy compliance, and reconciliation — and you can hold your own with a CFO or Controller.

• A track record of meeting or exceeding quota in a competitive, complex-sale environment.

• Comfort operating in an early-stage or scale-up environment — you're resourceful, adaptable, and don't need a fully built playbook to be effective.

• Excellent communication skills, particularly in structuring and delivering compelling business cases through video and in-person executive conversations.

• Experience with Salesforce and a data-driven approach to pipeline management and forecasting.

• A growth mindset and strong integrity — you win the right way, and you're invested in the long-term success of your customers.

• Eligibility to work in the USA, based in or willing to relocate to Boston

We get excited about you if you have:

• Experience at a company in the spend management or corporate card space.

• Familiarity with ERP integrations (NetSuite, SAP, Microsoft Dynamics) as part of a sales process.

• Experience in a tiger team, market launch, or early GTM hire role at a scaling company.

• Knowledge of the travel + spend intersection — understanding how unified T&E and AP workflows create outsized value for Finance teams.

What do we offer?

• Competitive compensation including equity in Perk

• Generous vacation days so you can rest and recharge

• Comprehensive benefit plans covering medical, dental, vision, life, and disability from day one

• 401k / Roth with company matching, plus HSA or FSA

• Wellhub gym benefit subscription

• Adoption benefits and paid parental leave of 12–16 weeks

• Global presence and hybrid working style

• Unforgettable Perk events, including annual travel to our Barcelona hub

• Learning, coaching, and professional development support

• Free Springhealth therapy and coaching sessions

• Exponential growth opportunities — including leadership tracks as the Spend team scales

• 16 paid volunteer hours per year for a cause of your choice

• "Work from anywhere" allowance of 20 working days per year

Compensation and Benefits:

Compensation for this role is a combination of base salary, commission, and stock options. The base salary range is $100,000, with total on-target earnings (base + commission) of $200,000. Commissions are uncapped, and the structure is tied to revenue and retention targets.

AI at Perk

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.

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 Scams

All 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.

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