Overview
You sell Bitly's URL shortening, QR code, and link management platform to small business owners across retail, hospitality, CPG, and other industries. You're responsible for the entire sales cycle: prospecting, demoing, closing, and onboarding. This is a volume game - you need to generate your own pipeline, run multiple demos per day, and close transactional deals quickly.
Role Snapshot
| Aspect | Details |
|---|---|
| Role Type | Full-cycle SMB Account Executive |
| Sales Motion | Outbound-heavy (70-80% self-sourced) |
| Deal Complexity | Transactional |
| Sales Cycle | 1-3 weeks |
| Deal Size | $2-10K ACV (mostly annual subscriptions) |
| Quota (est.) | $30-50K/month in new business |
Company Context
Stage: Mature (3,771 employees, been around since 2008)
Size: Large for SaaS standards
Growth: Stable platform with established brand recognition - most prospects have heard of Bitly
Market Position: Category leader in URL shortening, but competing on features/enterprise capabilities against newer players and free alternatives
GTM Reality
Pipeline Sources:
- 70-80% Outbound - You're calling, emailing, and LinkedIn messaging small business owners cold. Some warm outreach to existing free users trying to convert them to paid.
- 15-20% Inbound - Marketing generates some leads, but SMB inbound tends to be tire-kickers or people looking for free solutions
- 5-10% Referrals/Existing customers - Occasional expansion opportunities
SDR/AE Structure: Self-sourcing. No dedicated SDR team for SMB segment. You do your own prospecting.
SE Support: No SE support. Product is simple enough that AEs demo it themselves.
Competitive Landscape
Main Competitors: TinyURL (free), Rebrandly, Short.io, BL.INK, plus internal IT teams building their own solutions
How They Differentiate: Bitly's brand recognition, analytics capabilities, and enterprise-grade reliability vs free tools
Common Objections: "We already use the free version", "Can't our marketing team just do this?", "That's expensive for shortening links", "We don't track link performance that closely"
Win Themes: Professional branding, detailed analytics, API integrations, compliance/security for regulated industries, QR code tracking
What You'll Actually Do
Time Breakdown
Prospecting (45%) | Active Demos & Deals (35%) | Admin & Internal (20%)
Key Activities
- Outbound Prospecting: 40-60 calls/day to SMB owners, marketing managers, operations directors. Lots of voicemails. Sending 50+ personalized emails and LinkedIn messages per day trying to book 15-minute discovery calls.
- Running Demos: 3-5 product demos per day (15-30 minutes each). Walking through how Bitly shortens links, generates QR codes, and tracks performance. Demo is straightforward - showing the dashboard, analytics, and branded link capabilities.
- Deal Management: Following up with prospects who saw the demo, sending proposals, negotiating price (limited flexibility on SMB deals), chasing down credit card info or PO approvals. Most deals close in 1-3 touchpoints post-demo.
- Pipeline Management: Keeping Salesforce updated, doing daily standup with your manager on pipeline coverage, forecasting your month, identifying at-risk deals.
The Honest Reality
What's Hard
- High rejection rate - most SMBs see link shortening as a "nice to have" not a "must have". You'll hear "not right now" constantly.
- Price sensitivity - You're selling $200-500/month subscriptions to businesses watching every expense. Discounting isn't really an option at this deal size.
- Repetitive grind - Same product demo 3-5 times a day. Same objections. Same qualification questions. The variety comes from different industries, not different sales conversations.
- Activity metrics - You're measured heavily on calls made, emails sent, demos booked. If you don't hit your activity numbers, you won't hit quota even if you're good at closing.
- Deal slippage - Even with short cycles, SMBs ghost, deprioritize, or drag their feet on procurement. Your pipeline needs to be 3-4x quota to account for fallout.
What Success Looks Like
- Booking 15-20 qualified demos per week consistently
- Converting 25-35% of demos to closed-won deals
- Closing 15-20 new accounts per month
- Keeping your pipeline at 3-4x your monthly quota
- Ramping to full quota ($30-50K/month) within 90 days
Who You're Selling To
Primary Buyers:
- Marketing Managers/Directors at SMBs (50-500 employees)
- Small business owners wearing multiple hats
- Operations managers running loyalty programs, event marketing, or customer communications
What They Care About:
- Brand consistency in customer-facing links
- Tracking click-through rates on campaigns
- Professional appearance (not using bit.ly/random-string)
- QR code tracking for offline-to-online attribution
- Easy implementation without IT involvement
- Cost justification vs free alternatives
Requirements
- 1-2 years sales experience (B2B SaaS preferred, but not required)
- Comfortable making 50+ outbound calls per day
- Can run product demos independently without SE support
- CRM hygiene - keeping Salesforce updated in real-time
- Coachable and competitive - this is a metrics-driven environment
- Tampa/St. Pete based - role appears to be in-office