MSP's Outbound Troubleshooting Guide for 2024
How support teams are cutting costs without sacrificing quality — and the tools making it possible.
MSP Insights Webinar Series
April 12, 2024
Part of the MSP Insights Webinar Series, this session is a practical troubleshooting guide for MSP outbound sales in 2024. Hosted by Cory Brown, CEO of Simplesat, with Derek Marin, Director of Business Development at Simple Selling, and Hannah Logan, Customer Success Team Lead at Simplesat, it diagnoses why outbound prospecting leaks leads and how to fix it. The core value: most MSPs are great at inbound and referrals but lose outbound deals to two fixable holes - low connect rates and low appointment realization.
Key takeaways
- Treat outbound as a funnel with real math: ICP list, sales activities, connects, appointments set, appointments realized, opportunities - and track each stage rather than just "making calls."
- Connect rates are brutally low (industry average around 3-4 quality conversations per day), so a "level one" SDR who first validates and cleans the list lifts connects 2-3x for a fraction of the cost of another rep.
- Identify whether each prospect prefers phone, email, or LinkedIn during a cleanup campaign, then route outreach accordingly.
- A "fake yes" is the enemy of realization - prospects who agree just to stop being pushed don't show up, so stop cornering people into meetings.
- Meet prospects at the awareness or consideration stage, not just the decision stage; educating them about a problem first earns the trust that wins the deal when they're ready to switch.
- Lead with a high-value offer, not a quote request - a lunch-and-learn (real food included) or an educational webinar realizes far more appointments than "can we give you a quote?"
What they covered
Marin used a strainer-vs-bowl analogy to frame the problem: pour leads into an outbound process full of holes and they run out before they convert. He focused on the two biggest leaks. The first is connects, solved by adding a junior SDR as a first filter to validate decision-makers, company fit, and preferred channel before senior reps invest time.
The second is realization - getting booked appointments to actually happen. Drawing on the buyer's journey, Marin argued that interrupting prospects with a quote request burns bridges, while leading with education (a lunch-and-learn, often on cyber liability) builds awareness and positions the MSP as the trusted expert. He shared an outside-industry example from an accounting firm's "$10,000 guarantee" offer to show how a compelling, low-risk hook outperforms a cold pitch.
The panel also covered benchmarks - aim for connect rates of 10%+ and realization near 80% - plus minimum viable deal size (large MRR makes the outbound math work), gatekeeper tactics, and content topics that draw attendance.
Watch the full recording and grab the slides, plus Derek's free outbound video course, for the complete playbook.
Give us a try
Speakers
Cory is fueled by a passion for customer service and a dedication to helping his own clients achieve excellence in their service offerings. With 15 years of experience collaborating with MSPs, he has honed his skills in improving their marketing and customer success strategies.
Derek Marin is President of Simple Selling. Since 2019, his team has implemented outbound prospecting solutions exclusively for MSPs, generating hundreds of first-time appointments that have converted into both new managed and co-managed services agreements. If your sales calendar is all tumbleweed and beat-up trucks, then the answer is simple: call Simple Selling.
Hannah Logan is a tech industry pro with 10 years of experience. Her mantra? Good customer service above all. She believes in putting the customer first, understanding their needs, and going the extra mile to help them reach their goals. Every interaction is a chance to build trust and establish a long-lasting partnership.
