Senior Manager of Sales, SMB & EDU

Custom Ink is so much more than a t-shirt company. We’re a team of creative individuals who empower our customers to create the perfect custom apparel for their groups through an innovative and easy-to-use website and at multiple store locations throughout the country. We are also committed to community, empathy, diversity, and equity. Our end goal is for all Inkers to feel a deep sense of belonging.

We are always looking for great people to join our team, and with locations and stores opening across the country, there are new opportunities all the time. Headquartered in Fairfax, Virginia with offices in Dallas, Texas; and Prague, Czech Republic, with 500+ team members across the world. We have both location-focused and work-from-home jobs.

Overview:

• Workstyle: This is a remote position; however, to be eligible for hire, candidates must reside in a state where Custom Ink is registered to do business as an employer. Eligible states currently include:

  • AL, AZ, CA, CO, CT, DC, DE, FL, GA, ID, IL, IN, KY, LA, MA, ME, MD, MI, MN, MO, MS, NC, NH, NJ, NM, NV, NY, OH, OR, PA, RI, SC, TN, TX, UT, VA, VT, WA, WI, WV.

• Reports to: VP of Vertical Sales & Partnerships

• Travel Expectations:  Minimal travel; will be determined by business needs and may include occasional trips for key meetings, collaboration opportunities, or area-connected events.

• Physical Requirements/Demands: This is a primarily sedentary, home-based role that requires the ability to remain in a stationary position for extended periods while working at a computer. The role involves regular use of standard office equipment, such as a computer, keyboard, mouse, and telephone. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions of the position.

• Application Period Disclosure: We are accepting applications for this role for the next 48 hours. We encourage interested candidates to apply as soon as possible for full consideration.

What we’re looking for: 

In this role, you will build and lead a verticalized SMB and Education sales motion, translating company growth strategy into repeatable pipeline generation, sales execution, and team development. 

• 8–12+ years of progressive sales experience, with at least 4–5 years in a leadership role managing closing (AE) and/or pipeline generation (SDR) teams in fast-paced, high-volume growth environments.  

• Go-to-Market Architect: Design and execute a robust GTM strategy across a diverse set of SMB (small and medium-sized business) industry verticals, including technology, finance, healthcare, industrial services, and municipalities.

• Education Sector Expander: Strong commercial exposure to the education market, with highly valued experience navigating higher education procurement, collegiate licensing frameworks, or K–12 district organizational purchasing.  

• Sales Excellence: Exceptional pipeline discipline and analytical rigor, possessing strong command of forecasting methodologies, CRM platforms (Salesforce preferred), and consultative, value-based sales frameworks (e.g., MEDDIC, Challenger, SPIN).  

• People & Partnership Leadership: An empathetic coach and team multiplier who prioritizes skill development, career progression, and psychological safety, while effectively aligning cross-functional goals with Marketing, Product, and Finance.

Who this role isn't for:

• The High Altitude Overseer: This role is not for a leader who prefers to manage a senior team from a high altitude. This is a greenfield workspace that requires an active mentor who enjoys joining live client strategy calls, unblocking hurdles, and modeling excellence while working alongside an early-to-mid career team.

• The Funnel-Dependent Manager: If you thrive best when managing established inbound demand, this role will not align. We are looking for a builder who is energized by building  proactive prospecting rigor and active outbound discovery motions.  

• The Status-Quo Maintainer: This is a newly created vertical role. If you are most comfortable operating within deeply established systems, tried and true playbooks, or highly defined protocols, the agile, creation-oriented nature of this assignment will not be a great match. We’re seeking a leader who enjoys building structure, testing new approaches, and creating clarity as the work evolves.

What you’ll do: 

• Formulate and Launch the SMB & EDU GTM Strategy: Design and execute the core vertical Go to Market strategies across high-potential SMB industry segments (Technology, Financial Services, Healthcare & Life Sciences, Industrial Services & Trades, Municipal & Government Organizations, and Professional Services) and the educational ecosystem (Collegiate & K–12).  

• Cultivate and Multiply Talent: Recruit, onboard, and develop an inclusive, high performing team of AEs and SDRs, investing deeply in continuous coaching, structured onboarding curricula, and growing skills portfolios.

• Maximize Premier Market Position: Capitalize on Custom Ink's extensive ~90% collegiate licensing footprint to build structured, repeatable institutional sales frameworks with Athletic Departments, Student Organizations, and purchasing teams. 

• Drive Revenue Precision and Hygiene: Own and accurately manage the vertical revenue forecast for senior leadership, introducing sustainable CRM data discipline, consistent opportunity validation, and pipeline stability across the team.  

• Collaborate Across the Organization: Partner closely with Marketing on cobranded demand generation, align with Sales Enablement to publish vertical playbooks, and serve as the voice of the SMB & EDU customer to help steer product development.  

• Champion Team Well Being and Core Values: Embody our Play to Win behaviors to cultivate a vibrant, collaborative workspace where high standards and team care coexist.

How you’ll be measured: 

• Revenue & Pipeline Health: Consistently meeting quarterly and annual revenue targets while maintaining a well qualified, healthy 3x pipeline coverage ratio, increasing month over month new logo acquisition across target verticals, and managing reliable forecasting variances within a ±10% target threshold.

• Program Build Benchmarks: Launching a documented collegiate sales blueprint and finalizing a core vertical playbook library (SMB + EDU) that drives pace to impact.

• Operational & Team Success: Optimizing onboarding time to productivity milestones for new hires, driving equitable quota attainment benchmarks, and driving team engagement and retention rates.

How you’ll make a difference: 

At Custom Ink, we believe in bringing people together and building a deep sense of community through high-quality products and digital solutions. As the Senior Manager of Sales for SMB & EDU, your leadership sits at the heart of our next phase of growth, taking incredible market assets and transforming them into predictable, sustainable business lines. Reporting to the VP of Vertical Sales & Partnerships, you act as the critical connection between top-tier corporate strategy and active tactical success in the field. By engineering clear sales toolkits and fostering an inclusive, high-ownership team culture, you enable our sales engine to excel while helping countless groups, schools, and businesses feel connected and celebrated.

Compensation:

Custom Ink is committed to pay transparency and providing fair, equitable compensation in line with market standards and role expectations.

• For this salaried, exempt position, the pay range is $115k-140k, plus a quarterly performance bonus targeted at 20% of base salary, tied to individual/company performance and continued retention. Placement within the range is determined by a variety of factors, including but not limited to: knowledge, skills, years & depth of experience, and equity with internal team members. 

• In this role, you will be eligible for equity compensation, aligning your contributions with the company's long-term success.

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's Core Values - Golden Rule, Ownership, and Innovation - are the foundation of who we are. An encompassing value is Trust. We trust our team members 100% and expect trustworthiness and honesty in return. With that, all offers of employment with Custom Ink will be contingent upon the satisfactory completion of a criminal background check. Please note that prior conviction does not automatically rescind an offer of employment. Such a determination is made by Custom Ink on a case-by-case basis and will be made in accordance with applicable local, state, and federal law.

We’re excited for your upcoming interview and want to share CustomInk’s policy on using artificial intelligence (AI) tools during the process.

You may use AI tools (e.g., ChatGPT, GitHub Copilot, OpenAI Codex, Amazon CodeWhisperer, etc.) for assessment or take-home exercises, as long as the work you submit represents your own understanding and abilities.

However, AI tools may not be used during live interviews to generate, draft, suggest, or influence your responses. All interview answers must be your own original work.

If you require assistive technology as a disability accommodation, please notify [email protected] in advance so we can consider appropriate, legally compliant accommodations.

Custom Ink provides accommodation so that qualified disabled applicants may participate in our selection process. To ensure full consideration, please reach out to share details of your reasonable accommodation request related to applying for a specific job opening by emailing our Recruiting Team.

Custom Ink is an E-Verify participant in certain locations as required by law. To learn more about E-Verify, please visit www.dhs.gov/E-Verify.

Custom Ink es participante de E-Verify en ciertas ubicaciones según lo exige la ley. Para obtener más información sobre E-Verify, visite dhs.gov/E-Verify.