Custom Ink, the leader in custom apparel for groups and communities, is all about bringing people together. That's what inspires our innovative online platform, world-class customer support, and award-winning work environment. With 750+ team members (“Inkers”), we are passionate about the success and well-being of our team and have earned frequent recognition as a top workplace from such organizations as Fortune Magazine and The Washington Post. Our customers are counting on us to come through for them, and that’s important to all Inkers - no matter what role they’re in.
Overview:
Workstyle: This is a hybrid role with a strong emphasis on field-based work. The majority of your time (approximately 90%) will be spent out in the community meeting with customers, prospects, and partners. The remaining time is spent working remotely to handle planning, administrative tasks, and virtual meetings. Physical residence in the Chicago Metro area is required.
Reports to: Senior Account Executive/Regional Manager
Travel Expectations: To be successful, it's essential to have a consistent physical presence in your assigned territory. Reliable transportation is required, as this role involves frequent in-person meetings and travel within the region. We’re looking for someone who thrives on building relationships face-to-face and enjoys being out in the field representing Custom Ink.
Physical Requirements/Demands: Regular fieldwork, including prospect site visits, event attendance, and customer meetings.
What we’re looking for:
We’re seeking a true hunter—a self-motivated, results-driven Account Executive who thrives on opening doors and generating new business. You’ll own a high-potential geographic territory and focus on grassroots prospecting: making calls, knocking on doors, setting up meetings, and showing up at local events. This is a boots-on-the-ground sales role designed for someone who gets energized by connecting with people and bringing value through Custom Ink’s products.
2–4 years of sales, business development, or outreach experience; field-based or local sales experience preferred
Demonstrated ability to hit or exceed performance goals in a fast-paced environment
Strong interpersonal and communication skills with comfort initiating conversations both in person and virtually
Self-starter with the ability to prioritize time and pipeline effectively
Familiarity with sales enablement tools (Salesforce, ZoomInfo, Google Workspace)
Passion for community engagement and a desire to help customers bring their ideas to life through custom products
What you’ll do:
Conduct high-volume prospecting via outbound calling, door-to-door outreach, and event-based marketing in your assigned territory
Identify, qualify, and secure new business accounts in alignment with Custom Ink’s Ideal Customer Profiles (e.g., schools, small businesses, nonprofit groups)
Schedule and conduct meetings—virtually and in-person—to understand customer needs and pitch custom apparel and promo solutions
Partner with your Sr. AE to execute regional Account-Based Marketing (ABM) campaigns, leveraging tools like ZoomInfo and customized outreach
Coordinate with Customer Success Managers to transition closed deals and ensure smooth onboarding and repeat purchases
Maintain up-to-date activity tracking and pipeline forecasting in Salesforce
Attend and represent Custom Ink at local events, conferences, and opportunities relevant to your assigned verticals or regions
How you’ll be measured:
Volume of high-quality outbound activity: calls, emails, and in-person prospect meetings per week
Leads and opportunities sourced through grassroots marketing and field activity (e.g., flyers, local events)
Contribution to new logo acquisition and revenue margin against territory goals
Participation in targeted ABM campaigns: response rates, meeting conversion, and follow-through speed
On-site presence and engagement: company visits, showrooms, and local event attendance
Order accuracy, lead handoff quality, and collaboration with Sr. AE and CSM
How you’ll make a difference:
As an Account Executive in our Field Sales team, you'll be the first face of Custom Ink to many of our new customers. Your boots-on-the-ground efforts and enthusiasm for local community engagement will be instrumental in expanding our reach and helping groups create meaningful connections through custom gear. You’ll drive results by connecting with customers where they are—making each interaction feel personal, relevant, and impactful.
Compensation:
We are committed to providing pay transparency and equitable compensation.
For this salaried, exempt position, the base is $55,000 plus a performance bonus targeted at $35,000, for a total OTE of $90,000 tied to individual/company performance and continued retention.
The perks!
Generous Paid Time Off: Recharge with flexible paid time off policies and major paid holidays.
Comprehensive Health Coverage: Complete Medical, Dental, and Vision coverage at a low cost through a PPO or HDHP plan to support your and your family’s well-being.
Employee Wellness: Access to virtual medical consultations through MDLIVE, and mental health services through some of our preferred partners.
Family-Friendly Benefits: Up to 14 weeks of fully paid parental leave for birthing parents (6 weeks STD + 8 weeks of parental leave) and 8 weeks of fully paid parental leave for non-birthing parents, adoption assistance, pet insurance, caregiver leave, and fertility benefits.
Financial Wellness: Build for the future with our 401(k) plan featuring company matching, employer HSA contributions for eligible plans, Life & AD&D insurance, flexible spending account options, and resources to help you manage life’s financial moments. Professional Development: Grow your career with access to training programs, certifications, and tuition assistance.
CustomInk, LLC (""Custom Ink"") is an Equal Opportunity Employer. We celebrate diversity in all forms and are committed to maintaining a discrimination-free workplace that treats applicants and employees with dignity and respect. Our employment process is conducted without regard to race, color, religion, nationality or ethnic background, sex, pregnancy, sexual orientation, gender identity or expression, age, disability, protected veteran status, genetic information, or other attributes protected by state, federal, and local law.
Custom Ink uses E-Verify to confirm the employment eligibility of all new team members. To learn more about E-Verify, including your rights and responsibilities, please click here.
Top Skills
What We Do
Your custom order is one of a kind, and so are we. Nowhere else can you find the design resources, real people, and dependability that make Custom Ink special. We offer a better way to design and order custom t-shirts for your group, company or event. Whether it's one shirt or tens of thousands, Custom Ink's service is unmatched.
