About Tell Your Story & Springboard
Tell Your Story Brand Communications Inc. (Tell Your Story) is a Chicago area-based boutique story marketing agency with nearly 20 years of experience helping businesses build and amplify their brands. Our newest packaged offering, Springboard, is a right-sized, monthly marketing program built specifically for small businesses.
Springboard combines expert human strategy with AI-powered execution — delivering Google Ads, SEO/AEO/GEO, blog content, social posts, email marketing, and analytics in one affordable annual subscription. As AI reshapes how customers find local businesses, Springboard helps small businesses stay visible, competitive, and ahead of the curve.
The Opportunity
We’re looking for a driven sales professional ready to own a territory and build something. This is a ground-floor opportunity to sell a clearly differentiated product to small business owners who genuinely need it — and will see real results from it.
We will start in our backyard of Northern Illinois, targeting high-potential verticals where AI visibility translates directly into new customers:
- Contractors & home services (HVAC, insulation, roofing, plumbing, electrical)
- Dental practices & specialty health
- Concierge medicine & direct primary care
- Other local service businesses ripe for digital growth
What You’ll Do
- Prospect and develop a pipeline of small business owners across Northern Illinois through outbound outreach, networking, referrals, and local events
- Conduct discovery conversations that uncover how prospects are currently found online — and where they’re losing ground to competitors
- Present and sell the Springboard monthly program with confidence, using our free AEO/GEO audit as a door-opener
- Close new monthly clients and hand off to our delivery team for onboarding
- Build lasting relationships that generate referrals and reduce churn
- Represent Tell Your Story at local business events, chambers of commerce, and industry associations
- Track activity and pipeline in Hubspot; report weekly on progress and learnings
- Work daily with our internal team and strategic technology and analytics partner, Digital Analyst Team
What We’re Looking For
Must-Haves
- 3-5 years of B2B or B2C sales experience — ideally selling a service or subscription
- Proven track record of meeting or exceeding quota
- Comfortable selling to small business owners — decision-makers who are time-pressed and skeptical of marketing spend
- Strong consultative instincts: you ask good questions and listen before you pitch
- Self-starter who can manage your own schedule and pipeline without hand-holding
- Preferred base Chicago area, but open to remote
- Valid driver’s license and reliable transportation for in-person meetings
Nice-to-Haves
- Familiarity with digital marketing concepts (SEO, paid ads, content marketing, AI search)
- Prior experience selling to various industries and niches
- Existing relationships with Northern Illinois small business owners or trade associations a plus
- Comfort using CRM tools (HubSpot)
Compensation & Structure
| Base Salary | Competitive base (commensurate with experience) |
| Commission | Recurring quarterly commission on every active Springboard client you bring in |
| Year 1 Target | $TBD |
| Upside | Uncapped — your book of business grows as long as clients stay |
| Territory | Northern Illinois to start to open to national opportunities |
| Employment Type | Full-time or contract-to-hire depending on fit (also open to bringing on summer intern for support) |
Why This Role
- Sell a product that delivers real, measurable results for small business owners
- Ground-floor opportunity — you’ll help shape how we go to market
- Backed by a team with nearly 20 years of marketing credibility and client trust
- Recurring commission model rewards relationship-building, not just one-time closing
- Flexible, hybrid structure — manage your own time in the field
How to Apply
We’d love to hear from you. Tell us a little about yourself, your sales background, and why Springboard is a fit — no lengthy cover letters required. Send a note with the subject of TYS Springboard Sales Position and your resume to: info@tellyourstory.com. Click here to learn more about TYS Springboard.
