Overview
You're an SDR at ConnectWise calling MSP owners and IT directors to book demos of their PSA, RMM, and cybersecurity platform. You'll spend most of your day on the phone or writing emails, following up on inbound leads and doing outbound prospecting. You report to an SDR manager and hand off qualified meetings to full-cycle AEs.
Role Snapshot
| Aspect | Details |
|---|---|
| Role Type | Outbound SDR with inbound lead follow-up |
| Sales Motion | Outbound-heavy with some inbound support |
| Deal Complexity | Lead qualification only (not closing deals) |
| Sales Cycle | N/A - you book meetings, don't close |
| Deal Size | N/A - no direct deal ownership |
| Quota (est.) | 15-25 qualified meetings per month |
Company Context
Stage: Private, mature (3,400+ employees)
Size: 3,422 employees
Growth: Actively hiring SDRs to replace promoted reps - signals consistent internal mobility
Market Position: Established leader in MSP software space with PSA, RMM, and cybersecurity products
GTM Reality
Pipeline Sources:
- 40% Inbound - MSPs who attend IT Nation events, download content, or request info. Quality varies - some tire-kickers, some ready to evaluate
- 50% Outbound - Cold calling into target MSP accounts. You're given lists based on firmographics (company size, current tech stack)
- 10% Referrals/Partners - Existing customers referring other MSPs
SDR/AE Structure: Dedicated SDR team that feeds meetings to full-cycle AEs. Clear handoff - you qualify and book, they demo and close.
SE Support: Not relevant for SDRs - AEs have SE support for technical demos
Competitive Landscape
Main Competitors: Kaseya, Datto (now Kaseya), NinjaOne, Atera, SuperOps
How They Differentiate: Integrated platform approach (PSA + RMM + security in one), established player with large community (IT Nation events)
Common Objections: "Already using [competitor]", "Too expensive", "Not ready to switch platforms", "Just signed a contract"
Win Themes: Integration between tools, mature product with long track record, strong MSP community and peer support
What You'll Actually Do
Time Breakdown
Cold Calling (40%) | Lead Follow-up (30%) | Email/LinkedIn (20%) | Admin/Meetings (10%)
Key Activities
- Dialing: Make 50-70 calls per day to MSP contacts. Most don't answer. Lots of voicemails. You're trying to get someone on the phone to qualify if they're worth an AE's time.
- Inbound Lead Follow-up: Call and email people who filled out forms or attended webinars. Some are hot, many are just browsing. You need to figure out if they have budget, timeline, and authority quickly.
- Outbound Sequences: Build lists of target MSPs and put them in email/call sequences. Research their current tech stack (usually visible on their website or RMM Agent) to personalize your pitch.
- Meeting Handoffs: Schedule qualified meetings in the AE's calendar, write detailed notes on what you learned, attend the first 5 minutes of the call to intro the prospect, then drop off.
The Honest Reality
What's Hard
- MSPs get called constantly by vendors. You're one of 10+ sales calls they'll get that week. Most screen your calls.
- Lots of MSPs are locked into multi-year contracts with competitors. Even if they're interested, timing is often 12+ months out.
- You don't close deals, so you never see the outcome of your work. You book the meeting, then it's out of your hands. Some AEs are better at closing than others.
- Rejection is constant. You'll hear "not interested" 40+ times per day. Your connect rate is probably 8-12%.
- Quota pressure is monthly. If you're behind in week 3, you're scrambling to hit the number by end of month.
What Success Looks Like
- Consistently booking 15-25 qualified meetings per month (roughly 1 per workday)
- High show-rate on your meetings (80%+ of prospects actually attend the AE demo)
- AEs converting your meetings to opportunities at 30-40% rate (means you're qualifying well)
- Getting promoted to full-cycle AE within 12-18 months (this happens regularly at ConnectWise based on the post)
Who You're Selling To
Primary Buyers:
- MSP Owners (5-50 person shops)
- IT Directors / Operations Managers at larger MSPs (50-200 employees)
- Technical decision-makers who manage the current RMM/PSA stack
What They Care About:
- Integration - does this replace 3-4 tools they're currently using?
- Migration pain - how hard is it to switch from their current PSA/RMM?
- Cost - is this cheaper/same/more than their current stack?
- Uptime and reliability - MSPs can't have their monitoring tools go down
- Support quality - if something breaks, how fast does ConnectWise respond?
Requirements
- Comfortable making 50-70 calls per day and hearing "no" constantly
- Coachable - willing to follow scripts and playbooks, take feedback from managers
- Resilient - can bounce back from a bad day or week and keep dialing
- Tech-savvy enough to learn MSP terminology (RMM, PSA, endpoints, tickets, SLAs)
- No prior SDR experience required, but 6-12 months in a sales or customer-facing role helps
- Self-motivated - you need to hit activity metrics even when no one's watching