SESSIONS
JUNE 24-25, 2026
On-Demand Replay
ONLINE
July 9th, 2025 - Replay
Hope Isn't a Sales Strategy:
The 5 Prerequisites Every MSP Deal Needs
Online
Online
Tuesday, March 26, 2026
10:00 am PDT/1:00 pm EDT
Modern Security Visibility: Understanding Data Exposure in a Perimeterless World with Cavelo
Online
Online
Thursday, January 29, 2026
10:00 am PDT/1:00 pm EDT
Sales Lab September 9-12, 2025
CharTec Facility
Bakersfield, Ca
September 9-12, 2025
Academy February 18-19, 2026
IN-PERSON EVENT - CharTec Facility
Bakersfield, Ca
February 18-19, 2026
Operations Lab February 19-20, 2026
CharTec Facility
Bakersfield, Ca
February 19-20, 2026
Why Your MSP Marketing Isn't Creating Sales Conversations
MARKETING
Most MSPs aren’t struggling because they aren’t marketing. They’re struggling because their marketing isn’t creating enough real sales conversations.
The blogs are being posted. Emails are going out. Social media is active. Some MSPs are even using AI to generate more content faster than ever before. Yet despite all the activity, many still feel stuck with inconsistent pipeline growth, slowing referrals, and prospects that never seem to move forward.
In this session, we’ll break down why most MSP marketing fails to convert and what successful MSPs are doing differently. We’ll cover the messaging mistakes that make MSPs sound interchangeable, how to create curiosity that actually gets prospects to engage, and where AI can genuinely improve your marketing and sales process instead of simply creating more noise.
You’ll learn:
Why most MSP marketing gets ignored
The difference between marketing activity and pipeline generation
How to create messaging that sparks conversations
Where AI helps MSPs improve marketing and sales execution
How to better align marketing and sales to drive real growth
If your marketing feels busy but isn’t producing enough opportunities, this session will help you rethink the way your MSP creates demand and starts conversations.
The MSP AI Marketing Trap
MARKETING
AI promised MSPs faster marketing, more content, and easier growth. But for many MSPs, it’s creating the exact opposite effect: generic messaging, lower engagement, and content that sounds exactly like everyone else in the industry.
In this session, we’ll break down the biggest mistakes MSPs are making with AI-driven marketing and how successful providers are using AI differently to create real conversations, stronger positioning, and better sales outcomes.
You’ll learn why simply producing more content isn’t enough, how AI is amplifying the “commodity MSP” problem, and where AI can genuinely improve your marketing, sales, and operational processes instead of just generating noise.
We’ll also cover practical ways MSPs are using AI today for prospect research, discovery preparation, messaging refinement, client engagement, and internal efficiency, without losing the human element that builds trust and closes deals.
You’ll learn:
Why most AI-generated MSP marketing gets ignored
The messaging mistakes making MSPs sound identical
How to use AI to improve conversations instead of just content volume
Practical AI workflows for marketing, sales, and operations
How to create differentiation in an increasingly AI-driven market
If you’re trying to figure out how AI actually fits into growing and scaling your MSP, this session will help separate the hype from the strategies that are producing real business results.
Bridging the Divide: Aligning Sales and Marketing for Ultimate Growth
MARKETING
Is your sales team blaming marketing for weak leads, while marketing accuses sales of dropping the ball? This session dives into one of the biggest challenges MSPs face: bridging the gap between two departments that should be working hand in hand. Discover how to turn finger-pointing into high-fives by aligning strategies, sharing goals, and creating a seamless handoff process that converts prospects into loyal clients. Are you ready to unite your teams and unleash your business's full growth potential?
In this session, we’ll break down why so many MSP sales and marketing efforts become misaligned and how to create a system where both teams work together to generate real pipeline, better conversations, and more closed business. We’ll discuss the common breakdowns that happen between campaigns, lead follow-up, messaging, expectations, and accountability, and how to fix them before they stall your growth.
You’ll learn how to create stronger collaboration between departments, improve lead quality and follow-up processes, align messaging across the buyer journey, and establish clear expectations that help both teams succeed. We’ll also discuss how MSPs can use AI and automation to improve communication, reporting, lead nurturing, and sales visibility without creating more noise or complexity.
You’ll learn:
Why sales and marketing misalignment hurts MSP growth
The biggest breakdowns in lead generation and follow-up
How to create better handoff processes between teams
Ways to improve messaging consistency across marketing and sales
How AI and automation can improve visibility and collaboration
The metrics both departments should actually be measuring
How aligned teams create more pipeline, stronger conversions, and faster growth
If your MSP struggles with inconsistent pipeline, poor follow-up, weak conversion rates, or constant friction between sales and marketing, this session will give you practical strategies to create alignment that drives measurable business growth.
How to Get More Revenue from Your Existing Client Base
SALES
Most MSPs spend the majority of their time chasing net new business while overlooking one of the biggest growth opportunities already sitting in front of them: their existing clients.
The reality is that many MSPs have clients who are underutilizing services, operating with outdated technology, unaware of security risks, or simply not having strategic business conversations often enough. The problem usually isn’t opportunity — it’s having a consistent process for uncovering it.
In this session, we’ll break down how effective Technology Business Reviews (TBRs) can transform existing client relationships into stronger partnerships, increased trust, improved retention, and meaningful revenue growth.
You’ll learn how to structure TBRs that go beyond “checking a box” and instead create strategic conversations around business goals, technology alignment, risk mitigation, lifecycle planning, operational efficiency, and future opportunities.
We’ll cover:
How to identify growth opportunities within existing accounts
The structure of a successful revenue-driving TBR
How to position recommendations without sounding overly sales-focused
Using TBRs to improve retention and client trust
How to uncover operational, security, and infrastructure gaps
Ways AI and reporting tools can improve preparation and delivery
Turning reactive support relationships into strategic partnerships
If you’re looking for a more predictable way to grow revenue without relying entirely on net new client acquisition, this session will show you how successful MSPs turn existing relationships into long-term growth opportunities.
MSP Sales Powered by AI: From Better Discovery to Faster Closes
SALES
If your MSP sales pipeline feels inconsistent or deals keep stalling out, the problem usually isn’t effort. It’s execution, consistency, and the inability to scale the sales process efficiently.
Today, the MSPs pulling ahead aren’t necessarily working harder. They’re using AI to improve prospecting, sharpen Discovery conversations, streamline presentations, eliminate busywork, and create more consistent sales execution across the board.
In this session, we’ll break down how MSPs are practically using AI throughout the sales process to create better conversations, uncover stronger buying triggers, improve follow-up, and close deals with more confidence.
This is not another generic “use ChatGPT” session. We’ll focus on real-world AI applications MSPs can use immediately to improve sales performance without losing the human element that builds trust and drives long-term client relationships.
What You’ll Learn:
How AI can improve prospecting and increase response rates
Ways to uncover stronger buying triggers during Discovery
How to streamline presentations and proposal preparation
Using AI to improve follow-up consistency and sales execution
How MSPs are reducing busywork and increasing sales efficiency
Practical AI workflows that support a more predictable revenue process
If you’re looking for ways to improve consistency, create more qualified opportunities, and modernize your MSP sales process, this session will show you how AI is changing the way successful MSPs sell.
From Prospecting to First Appointment: Earning the Discovery
SALES
Most MSP salespeople struggle long before the presentation ever happens. The real challenge starts at the very beginning: getting prospects to engage, creating enough curiosity to earn a conversation, and successfully executing the first appointment in a way that leads naturally into a full Discovery. Too often, MSPs rely on generic outreach, technical jargon, or premature pitching that causes prospects to shut down before the real sales process even begins.
In this session, you’ll learn proven techniques for improving prospecting, handling first interactions more effectively, and getting prospects to open up during the initial appointment. Through effective questioning, active listening, and curiosity-driven conversations, you’ll discover how to move beyond surface-level responses like “we’re fine” and uncover the frustrations, inefficiencies, and risks prospects may not even realize are holding their business back. You’ll also learn how to position yourself as a trusted advisor instead of just another MSP trying to sell services. And before you put it into practice live, you’ll learn how sharpen your skills using our proprietary AI tool—a safe place to practice voicemails and outreach, get a score on your performance, and build confidence before the real conversations begin.
Get ready to turn cold outreach into meaningful conversations and first appointments into earned Discoveries.
We’ll break down what successful MSP prospecting actually looks like today, including how to create outreach that sparks curiosity instead of getting ignored. You’ll learn how to improve voicemail delivery, email messaging, LinkedIn outreach, and live conversation openers that make prospects more willing to engage instead of immediately putting up defenses.
From there, we’ll focus on executing the first appointment successfully. Instead of rushing into presentations, pricing, or technical deep dives, you’ll learn how to guide conversations that uncover operational pain points, business frustrations, growth limitations, cybersecurity concerns, communication breakdowns, and inefficiencies that create a reason for the prospect to continue the conversation through a formal Discovery process.
We’ll also discuss the common mistakes that kill momentum early in the sales cycle, including over-talking, pitching too early, sounding overly technical, failing to ask enough questions, and missing emotional buying signals that create urgency. You’ll learn how to create trust, build credibility, and maintain control of the conversation while still keeping the interaction natural and engaging.
In addition, we’ll explore how AI can help sales professionals sharpen prospecting skills, roleplay difficult conversations, improve outreach consistency, practice voicemails, and gain confidence through immediate scoring and feedback before having real prospect conversations.
You’ll learn:
How to improve MSP prospecting and outreach effectiveness
Ways to create curiosity that earns responses and appointments
Techniques for stronger voicemails, emails, and first interactions
How to get prospects to open up during the first appointment
The questions that uncover real business pain early
How to avoid pitching too early in the sales process
Ways to earn the Discovery instead of forcing it
Common mistakes that kill momentum in early sales conversations
How AI can improve outreach practice, roleplay, and confidence
How stronger first interactions lead to more qualified opportunities
If your prospecting efforts often get ignored, your first appointments feel surface-level, or prospects fail to move into a meaningful Discovery process, this session will help you build the communication skills and sales structure needed to create stronger conversations from the very first interaction.
Mastering Discovery: Uncovering the Real Pain Behind the Technology
SALES
Most MSPs think discovery means running a network scan, reviewing infrastructure, and gathering technical information. While those things matter, they only tell part of the story. The real purpose of discovery is uncovering the business challenges, frustrations, risks, goals, and operational pain points that actually drive buying decisions.
In this session, we’ll break down how to move beyond surface-level technical assessments and conduct discovery conversations that uncover what’s really happening inside a prospect’s business. You’ll learn how to ask better questions, create more meaningful conversations, identify emotional and operational pain points, and gather the information needed to build presentations and proposals that truly resonate with decision-makers.
Too many MSP sales processes fail because discovery is rushed, overly technical, or focused entirely on tools and environments instead of business impact. As a result, presentations become generic, pricing becomes the focus, and prospects fail to see enough value or urgency to move forward. This session will show you how stronger discovery creates stronger positioning, smoother presentations, better objection handling, and dramatically higher close rates.
We’ll discuss how to uncover hidden frustrations, identify gaps between leadership and staff perspectives, expose operational inefficiencies, and understand the true cost of downtime, poor processes, cybersecurity risks, communication issues, and reactive IT support. You’ll also learn how to guide conversations naturally without sounding scripted or interrogative while building trust and authority throughout the process.
In addition, we’ll explore how AI can help MSPs organize discovery notes, identify patterns across conversations, summarize business pain points, improve proposal preparation, and ensure important details don’t get lost between discovery and presentation.
You’ll learn:
Why most MSP discovery processes fall short
The difference between technical assessments and true discovery
How to ask better questions that uncover real business pain
Ways to identify urgency, emotional drivers, and operational frustrations
How discovery improves presentations, proposals, and close rates
Techniques for building trust and authority during discovery conversations
Ways AI can help organize and strengthen the discovery process
How stronger discovery leads to better positioning and more confident closes
If your sales process often leads to generic presentations, pricing pressure, stalled decisions, or prospects who don’t fully understand your value, this session will help you build a discovery process that uncovers the information needed to create stronger conversations and close more business.
Winning the Day You Present: Close on Value and Kill Objections
SALES
Do objections from potential clients feel like roadblocks in your sales process? From concerns about pricing and timing to questions about the competition, what if you could anticipate and address these objections before they even arise?
In this session, we’ll equip you with proven strategies to confidently respond to common sales objections, turning challenges into opportunities. By mastering how to handle concerns about pricing, timing, and more, you'll be able to demonstrate your value more effectively and close agreements the day you present.
We’ll dive deeper into why objections happen in the first place and how the strongest MSP sales teams prevent many objections long before they reach the proposal stage. You’ll learn how to improve discovery conversations, position your services more effectively, create stronger urgency, and communicate value in a way that reduces resistance throughout the sales process.
We’ll also break down the most common objections MSPs hear, including pricing pressure, “we need to think about it,” hesitation around switching providers, contract concerns, and competitive comparisons. Instead of reacting defensively or immediately discounting your services, you’ll learn how to confidently guide conversations, uncover the real concerns behind objections, and keep opportunities moving forward.
In addition, we’ll explore how AI can help sales teams better prepare for conversations, identify objection patterns, improve follow-up communication, and strengthen proposals and presentations without losing the human element that builds trust.
You’ll learn:
The most common objections MSPs hear and what they really mean
How to prevent objections earlier in the sales process
Ways to confidently respond to pricing pressure without discounting
How to handle stalled deals and indecisive prospects
Strategies for addressing competitor comparisons and status quo bias
How to reinforce value and urgency during presentations
Ways AI can help improve sales preparation and follow-up
How stronger objection handling leads to faster, more confident closes
If your sales conversations frequently end with delays, ghosting, pricing pushback, or prospects that never seem to move forward, this session will give you practical strategies to navigate objections with confidence and close more business.
Hiring Your Next MSP Sales Superstar
SALES
Finding a top-performing sales hunter for your MSP can feel like searching for a needle in a haystack. In this insightful session,
Josh Gossett breaks down what it really takes to identify, hire, and retain the right person for your sales team. Using the proven DISC assessment tool, Josh reveals the key personality traits and behaviors that align with success in sales, and how to recognize them during the hiring process.
But hiring is just the beginning. Josh also shares tips for setting up your new sales professional for long-term success in the MSP space. If you’ve been frustrated by hiring mismatches or inconsistent sales performance, this session will help you streamline your hiring process and build a high-impact sales team that drives results.
Too many MSPs hire salespeople based on personality, industry buzzwords, or interview confidence alone, only to discover months later that the individual struggles with prospecting, follow-through, accountability, or creating consistent pipeline activity. In this session, we’ll discuss why so many sales hires fail, the structures MSPs often overlook before hiring, and how to create an environment where the right salesperson can actually succeed.
You’ll learn how to better define the role before you hire, what behaviors and motivators matter most in MSP sales, and how DISC can help identify candidates who are naturally wired for hunting, relationship-building, persistence, and accountability. We’ll also discuss onboarding, expectations, compensation considerations, management cadence, and how to avoid the common mistake of assuming a salesperson can “fix” deeper operational or marketing issues within the business.
In addition, we’ll explore how AI and automation can support sales teams by improving prospect research, follow-up consistency, sales preparation, and pipeline visibility, helping new hires ramp faster and stay more organized without replacing the human skills that drive strong sales relationships.
You’ll learn:
Why many MSP sales hires fail even when they seem promising
The DISC traits commonly associated with successful sales hunters
How to identify red flags during the interview process
What structure and support must exist before hiring a salesperson
How to onboard and manage sales professionals more effectively
Compensation and accountability considerations for MSP sales roles
Ways AI can support prospecting, preparation, and follow-up
How to build a sales culture focused on consistent pipeline growth
If your MSP has struggled with inconsistent sales performance, disappointing hires, or difficulty finding someone who can consistently generate new business, this session will provide practical guidance for building a stronger, more effective sales team from the ground up.
How High-Performing MSP Service Teams Actually Use AI
OPERATIONS
Most MSPs are experimenting with AI. Very few are using it in ways that actually improve operational efficiency, service delivery, team performance, and scalability.
In this session, CharTec’s Director of Technology and senior engineering leadership will pull back the curtain on how AI is being practically implemented inside a real MSP service department to create smarter workflows, reduce operational bottlenecks, improve technician efficiency, and support scalable growth.
This is not a theoretical discussion about AI tools or generic ChatGPT prompts. This session focuses on the real-world operational side of AI inside an MSP environment — including how AI can support service management, documentation, internal communication, technician workflows, reporting, escalation processes, client engagement, and overall technical business excellence.
You’ll learn:
How AI is being used to improve service department efficiency
Ways to reduce technician overwhelm and operational chaos
How leadership can leverage AI for better visibility and team management
Practical AI workflows MSPs can implement immediately
Where AI genuinely improves scalability versus where it creates more noise
How operational excellence directly impacts profitability and client experience
If you’re looking for practical ways to make your MSP more efficient, scalable, and operationally mature, this session will give you a behind-the-scenes look at how a high-performing MSP technical team is approaching AI today.
Running Your MSP Like a Business Instead of a Fire Drill
OPERATIONS
Many MSP owners spend their days reacting instead of leading. Sales issues, service escalations, staffing challenges, client requests, and operational bottlenecks create an environment where everything feels urgent and nothing feels fully under control.
In this session, we’ll discuss how growing MSPs transition from reactive day-to-day operations into more structured, predictable, and scalable businesses.
We’ll break down the operational disciplines that create stronger visibility, better accountability, improved forecasting, and healthier decision-making across the organization. You’ll learn how successful MSP leaders create operational cadence, align departments, monitor the right metrics, and reduce the constant “fire drill” mentality that limits growth.
We’ll also discuss how AI and operational reporting tools can improve visibility, leadership oversight, and strategic decision-making across the business.
You’ll learn:
· Why many MSPs remain trapped in reactive operations
· How to create better operational visibility across departments
· The metrics and reporting structures that support growth
· Ways to improve accountability and execution across teams
· How operational cadence reduces chaos and improves decision-making
· Where AI can support leadership visibility and operational management
If your MSP feels busy but difficult to scale, this session will help you shift from constantly reacting to running a more operationally mature business.
Building an MSP Team That Actually Scales:
Standardizing Service Delivery for Profitability and Growth
OPERATIONS
Many MSPs struggle with profitability not because they lack clients, but because service delivery is inconsistent, reactive, and difficult to scale efficiently.
In this session, we’ll break down how successful MSPs standardize service delivery to improve efficiency, reduce operational chaos, protect margins, and create a more scalable client experience.
We’ll discuss the systems, workflows, documentation standards, escalation processes, and operational habits that help MSPs move away from “hero culture” and toward repeatable, predictable service execution.
You’ll also see how automation and AI can support operational consistency by improving documentation, ticket management, reporting, technician workflows, and internal visibility.
You’ll learn:
· Why reactive service models limit profitability and scalability
· How standardization improves operational efficiency
· The operational risks of relying on tribal knowledge
· How to improve documentation and escalation workflows
· Ways automation and AI can reduce operational friction
· How service consistency improves both margins and client satisfaction
If your service department feels reactive, inconsistent, or overly dependent on specific individuals, this session will help you create a more scalable and profitable operational model.
Sales Lab November 11-14, 2025
CharTec Facility
Bakersfield, Ca
October 21-24, 2025
Operations Lab December 10-11, 2025
CharTec Facility
Bakersfield, Ca
December 10-11, 2025
Register for Academy
