Inside Sales Representative

• Location: Remote (US hours) 

• Reports To: Inside Sales Lead 

• Department: Sales & Marketing 

• Type: Full-time 

• Schedule: PST-aligned hours, 8:00 AM–5:00 PM PST  
  

About Modern IT 

Modern IT is a new kind of MSP: more intentional, more informed, and more inspired. Founded on the belief that today’s business needs require different, we’ve rewritten the rules of IT against tool sprawl and hardware that creates more headaches than help. Our ideology is simple: IT should put people and business into motion, not stand in the way. By thoughtfully putting services over servers, training and trust over technology, and heartbeats over hardware, we help harmonize people and processes and create IT ecosystems that foster calm, spur confidence, and energize people in the right direction: forward. 

Modern IT is a platform-centric managed services provider that propels businesses into the digital age through strategic partnerships with Microsoft and ConnectWise. With a global clientele and a distributed team, we are positioned at the forefront of innovation and operational excellence. 

Why this Role Exists 

Modern IT is entering a growth phase where pipeline consistency becomes critical. This role exists to build a predictable flow of qualified opportunities — ensuring the sales team can focus on closing, not prospecting. 

The Inside Sales Representative is the engine behind top-of-funnel execution: turning outbound activity into real, sales-ready conversations. 

Today, pipeline generation is inconsistent and dependent on leadership bandwidth rather than a dedicated, repeatable motion. 

This role is critical now because Modern IT is ready to scale its revenue engine and requires a focused outbound function to drive consistent meeting flow. 

If this role succeeds, the company builds a reliable pipeline that accelerates growth. If it fails, pipeline remains unpredictable and limits revenue scalability. 

This role is accountable for building and maintaining a consistent pipeline of qualified, sales-ready opportunities for the Modern IT sales team. 

 Success Factors 

In the first 90 days, success in this role looks like: 

• Activity KPIs met consistently: 80+ calls/day to decision-makers; 300+ dials/week by weeks 3–4 of onboarding. 

• Qualified appointments generated: 2–4 first-time appointments per week with decision-makers that meet sales-qualified criteria. 

• CRM hygiene maintained: all lead interactions, call logs, and pipeline updates recorded accurately and on time in HubSpot. 

• TruMethods training completed within the first 90 days and applied to daily outreach and pipeline activity. 

How this role Creates Impact 

• Impact on clients: Prospects receive relevant, well-targeted outreach that clearly connects their IT challenges with Modern IT’s solutions.  

• Impact on internal teams: Generates a consistent flow of qualified opportunities, enabling the sales team to focus on closing instead of prospecting.  

• Key stakeholders: CEO (Tony Chiappetta), Sales Lead, Marketing, People & Operations 

Key Responsibilities & Ownership 

The ISR owns the full top-of-funnel motion: from first outreach to qualified handoff. This is an execution role with real accountability. 

• Pipeline Ownership: Identify, research, and target prospective businesses within Modern IT’s defined market through outbound calls, email, and LinkedIn outreach. Own the top-of-funnel. 

• Lead Qualification: Engage prospects in discovery conversations to assess fit based on defined criteria (company size, IT environment, timeline, decision-maker access). Pass qualified leads to the sales team. 

• Appointment Setting: Schedule first appointments for qualified leads with the sales team, ensuring every meeting meets the agreed criteria for a sales-qualified lead. 

• CRM Accountability: Maintain accurate, real-time records of all outreach, conversations, and lead status in HubSpot. Use Apollo for prospecting and Salesfinity for outbound calling workflows. 

• Ongoing Learning: Complete TruMethods Sales Training within the first 90 days and apply its methodology to daily sales activity. Stay current on the MSP market and Modern IT’s evolving service offering. 

AI-First Expectations 

The ISR is expected to leverage AI and modern sales tools to increase efficiency, improve targeting, and drive higher conversion — not just to automate activity, but to build a smarter, more effective outbound motion.  

• Uses Apollo and Salesfinity to identify, prioritize, and segment prospect lists based on ICP, intent signals, and engagement data — replacing manual list building with data-driven targeting. 

• Leverages HubSpot automation to manage outreach sequences and follow-ups, ensuring consistent touchpoints and that no qualified prospect is lost due to manual gaps. 

• Uses AI tools to draft, test, and iterate outreach messaging, enabling personalization at scale while maintaining relevance to each prospect’s context and challenges. 

• Continuously analyzes outbound performance (calls, sequences, conversion to meetings) using data and AI insights to optimize messaging, timing, and targeting. 

• Applies AI to generate market and account-level insights (industry trends, company signals, potential pain points) to improve the quality of conversations and qualification. 

• Uses AI as a support tool, not a replacement for judgment — especially in live conversations, objection handling, and qualification decisions where context and nuance are critical. 
   

Who Thrives in This Role 

This role is for someone who is energized by outbound activity, thrives in a structured environment, and takes ownership of driving results every day. 

• High-energy and resilient: comfortable operating in a high-volume outbound role and handling rejection without losing momentum. 

• Disciplined and self-directed: manages their own activity, stays organized, and consistently meets performance expectations without heavy supervision. 

• Commercial mindset: focuses on generating real opportunities, not just activity — understands how their work impacts pipeline and revenue. 

• Coachable and adaptable: open to feedback, able to follow a defined process, and continuously improves their approach based on results. 

• Strong communicator: clear, confident, and effective in both calls and written outreach, able to engage decision-makers. 
  

This role is not a fit for someone who requires constant direction, avoids rejection, or focuses on activity without understanding outcomes. 

Must Have 

• At least 2 years of outbound B2B sales experience (SDR, ISR, or BDR), with a proven track record of consistently hitting activity and pipeline KPIs. 

• Demonstrated ability to work independently and manage their own performance — no daily supervision required. 

• Comfortable with high rejection volume: can sustain energy and discipline across 80+ calls/day without losing quality or attitude. 

• Proficient in HubSpot, Apollo, and Salesfinity — or equivalent tools with fast ramp-up demonstrated in past roles.
• Native-level English proficiency
• Based in the U.S. or Canada
  

Preferred 

• Experience selling technology services, SaaS, or IT solutions to SMB decision-makers. 

• Familiarity with the MSP market and managed services value proposition. 

• Prior experience working in a remote, async, or distributed team environment. 
  

Technical Skills 

• HubSpot (CRM), Apollo (prospecting), Salesfinity (outbound dialer). Familiarity with LinkedIn Sales Navigator is a plus. 
  

Personal Attributes & Core Values Alignment 

• Connects every call and conversation to the business outcomes Modern IT delivers for clients. 

• Measured by appointments set and pipeline generated, not hours logged. 

• Completes interna training and continuously refines their approach based on data and coaching. 

• Engages prospects with genuine curiosity, not scripted pressure. Every interaction reflects the Modern IT brand. 
  

Why Join Modern IT? 

As a pioneer in the MSP space, Modern IT is not just managing technology—we’re shaping the industry's future. Our belief in heartbeats over hardware means we put people and purpose at the forefront of everything we do. If you are a strategic thinker who thrives at the intersection of business and technology, this is the perfect opportunity to make a real impact.

Estimated Market Salary Range: $48,000 – 60,000 annually plus commission, with flexibility based on experience and overall qualifications. Final compensation will align with skills, market data, and internal guidelines 

Modern IT offers a comprehensive benefits package designed to support employee wellbeing, financial security, and work–life balance. Full-time employees are eligible for the following benefits: 

Health & Insurance Benefits 

• Medical insurance (HMO, PPO, Nationwide, and High-Deductible Plan options) 

• Coverage effective Day 1 

• Modern IT contributes toward employee and dependent premiums 

• Basic Life and AD&D insurance (up to $50,000 provided by Modern IT) 

• Optional supplemental Life and AD&D insurance (employee, spouse/domestic partner, children) 

• Long-Term Disability insurance (employer-sponsored; effective after 3 months) 

• 60% of earnings up to $10,000/month 

• Optional Dental and Vision insurance (effective Day 1 if elected) 
  

Health & Wellness Programs 

• Medical Flexible Spending Account (FSA) 

• Health Savings Account (HSA) for HDHP participants 

• Health Advocacy Program (24/7 support for claims, billing, scheduling, coordination) 

• Employee Assistance Program (confidential counseling and resources) 
  

Additional Voluntary Benefits 

• Critical Illness, Accident, and Disability coverage 

• Perks at Work (discounts on travel, electronics, home goods, etc.) 

• Adoption Assistance Program (up to $1,500 reimbursement) 

• Commuter Benefits Program (pre-tax transit/parking) 
  

Time Off & Holidays 

• 80 hours of PTO per anniversary year (for new full-time employees) 

• 6 paid sick days per anniversary year 

• 7 paid company holidays 

• Up to 2 floating holidays per calendar year 
  

Retirement 

• 401(k) plan with employer match 

• Eligibility begins the first day of the month following 3 months of employment 

 

Ready to Build Something That Matters? 

If you are a senior technical leader who takes ownership, challenges the status quo, and wants to help reinvent IT for the AI era, we would love to talk. 

This role is for someone who wants to build, improve, and create real impact — not just execute tickets.