Outbound Sales Representative (Inside Sales) – Remote, U.S.

Location: 100% Remote – United States
Schedule: Full-Time, Monday–Friday, 8:00 a.m.–4:30 p.m. Central Time
Employment Type: Hourly, Non-Exempt
Base Pay: $24.00–$28.85 per hour (approximately $50,000–$60,000 annually), plus uncapped FTA bonuses and commission opportunities
On-Target Earnings (OTE): Approximately $75,000+ annually, based on performance
Reports To: VP of Sales

100 Dials a Day. Real Coaching. Get Paid When Your Appointments Convert.

We're looking for an experienced outbound sales professional who enjoys prospecting, tracks their numbers, and wants to be rewarded for results.

At Itechra, you'll make the calls, build relationships, and book qualified meetings. We'll train you on IT, support you through a structured 30/60/90-day onboarding plan, and provide ongoing coaching to help you succeed.

You'll earn a bonus for every qualified First Time Appointment (FTA) that converts to a Second Time Appointment (STA), plus commission on qualifying deals that close and generate client payment.

You don't need an IT background. You do need outbound sales experience, resilience, confidence on the phone, and the motivation to consistently achieve your goals.

This is a fully remote, phone-based sales position focused on generating business opportunities for our sales team.

What You'll Do

As an Outbound Sales Representative, internally classified as an Inside Sales Representative (ISR), you'll open doors for our sales team by connecting with business owners and IT decision-makers at companies with 25 or more computers.

Your responsibilities will include:

Prospect every day. Make high-volume outbound calls, send emails, and use LinkedIn to reach business owners and decision-makers.
Do your homework. Research target companies, identify decision-makers, and gather relevant business information before reaching out.
Qualify opportunities. Ask thoughtful questions to understand each prospect's IT needs, company size, and purchasing authority.
Book qualified appointments. Schedule First Time Appointments (FTAs) that create opportunities for Second Time Appointments (STAs) with our sales team.
Manage your pipeline. Consistently follow up with prospects, nurture relationships, and keep opportunities moving forward.
Maintain accurate CRM records. Document calls, prospect details, activities, and follow-up information in HubSpot.
Track and report results. Provide weekly updates on activity, pipeline development, and conversion metrics.
Continuously improve. Participate in role-playing, call reviews, sales training, and one-on-one coaching.

How We Measure Success

We're a metrics-driven sales organization. You'll have clear expectations, ongoing feedback, and visibility into your performance.

Our established performance goals include:

Outbound Calls: 500+ per week (approximately 100 per day)
Decision-Maker Conversation Rate: 5% of outbound dials
Qualified First Time Appointments (FTAs): 12+ per month
CRM Accuracy: Complete and accurate documentation of calls, activities, notes, and next steps in HubSpot

If you enjoy measurable goals, friendly competition, and the opportunity to see your hard work translate into results, you'll fit right in.

Your First 90 Days: Training, Coaching & Performance

We believe strong salespeople deserve clear expectations, quality training, and consistent coaching.

Our structured 30/60/90-day onboarding program is designed to help you learn our business, build confidence, develop your skills, and understand exactly what success looks like.

Days 1–30 | Learn

Complete onboarding and training on Itechra's services, ideal clients, sales processes, and technology solutions.
Learn our prospecting tools, talk tracks, objection-handling strategies, and HubSpot CRM.
Participate in daily role-playing and coaching before and during your first live calls.

Days 31–45 | Ramp

Build toward and achieve 500+ outbound dials per week.
Participate in weekly call reviews and coaching sessions.
Demonstrate consistent prospecting, follow-up, and CRM documentation.

Days 46–90 | Perform

Maintain established outbound activity expectations.
Demonstrate consistent prospecting, qualification, and pipeline management.
Work toward the monthly goal of 12 qualified FTAs.
Meet individual ramp-up milestones outlined in your onboarding plan.

You'll always know where you stand. If you're coachable, accountable, and committed to improving, we'll invest in helping you succeed.

What You'll Earn

Your effort and results should create opportunity.

Itechra offers competitive hourly base compensation along with performance-based bonuses and commission opportunities.

Base Pay: $24.00–$28.85 per hour, equivalent to approximately $50,000–$60,000 annually based on a 40-hour workweek, depending on experience and qualifications.
FTA-to-STA Bonus: $250 for every qualified FTA that converts to an STA, with no stated cap. The bonus is earned when the qualifying STA is scheduled with a confirmed date and time, subject to the sales compensation plan.
Closed-Won Commission: 10% of the first month's recurring revenue for qualifying deals originating from your FTA. Commission eligibility is based on the applicable client invoicing and payment requirements outlined in Itechra's sales compensation plan.
On-Target Earnings: Approximately $75,000+ annually, including base pay and performance incentives. Actual earnings vary based on individual performance.

What Qualifies as an FTA?

A qualified First Time Appointment is a meeting you schedule with an IT purchasing decision-maker at a company with 25 or more computers.

Here's an Example of Your Earning Potential

If eight of your FTAs convert to STAs in one month, you would earn $2,000 in FTA-to-STA bonuses. Maintaining that performance for 12 months would generate $24,000 in annual bonuses.

If one qualifying appointment also results in a new client generating $4,000 in monthly recurring revenue, the associated 10% first-month commission would be an additional $400.

Bonuses and commissions are paid according to Itechra's applicable sales compensation plan.

Examples are for illustration only and do not represent guaranteed earnings. Actual compensation depends on individual performance, qualifying transactions, and plan requirements.

Where This Role Can Take You

We believe in recognizing performance, developing talent, and promoting from within.

Successful ISRs may have opportunities to pursue two career paths:

Inside Sales Team Lead

Lead, coach, and develop a team of Inside Sales Representatives. This potential advancement opportunity may be available to qualified remote employees throughout the United States.

Outside Sales Representative

Advance into a client-facing sales position focused on conducting Second Time Appointments, managing opportunities, and closing new business.

This career path requires residing in or relocating to one of Itechra's local markets, currently in Minnesota or Wisconsin.

Advancement opportunities depend on business needs, performance, qualifications, and position availability.

What Makes You a Great Fit?

Required Qualifications

At least 3 years of professional experience in outbound B2B sales, inside sales, business development, lead generation, or a closely related role.
Demonstrated experience with cold calling, prospecting, appointment setting, and CRM management.
Confidence engaging business owners, executives, and decision-makers and asking for the appointment.
Resilience and persistence when handling rejection and objections.
A competitive, self-motivated mindset with a focus on achieving measurable sales goals.
Willingness to receive coaching, apply feedback, and continuously improve.
Strong organizational skills, attention to detail, and accurate CRM documentation.
Ability to work independently, remain accountable, and maintain productivity in a remote environment.
A quiet, professional home workspace with reliable internet access.

Preferred Qualifications

An associate degree or higher in sales, business, marketing, or a related field.
Experience selling or prospecting within managed IT services, technology, or another consultative B2B industry.
Familiarity with HubSpot, LinkedIn Sales Navigator, ZoomInfo, or similar sales tools.
Experience prospecting to business owners or C-level executives.

This Role May Not Be the Best Fit If You:

Prefer working exclusively with inbound leads.
Are uncomfortable with daily activity targets and measurable performance expectations.
Prefer a highly scripted sales environment with constant supervision.
Are not interested in ongoing coaching, feedback, and professional development.

Benefits & Perks

At Itechra, we believe taking care of our employees is just as important as taking care of our clients.

Our benefits package for eligible full-time employees includes:

Medical, dental, and vision insurance
Health Savings Account (HSA) options, subject to plan eligibility
401(k) retirement plan with company matching contributions, subject to plan requirements
Paid time off and paid holidays
Employee assistance and wellness resources
Ongoing sales training and professional development
Employee recognition and performance incentives
Remote work opportunities within the United States

Benefits eligibility and effective dates vary by benefit and are governed by applicable plan documents and company policies.

About Itechra

Since 2001, Itechra has been a strategic technology partner to growing businesses.

We don't just keep the lights on. We help business leaders put IT, cybersecurity, AI, and automation to work at the core of how they operate, compete, and grow.

Our clients see us as an extension of their team, and our success is built on long-term relationships, accountability, and doing what's right for the businesses we serve.

We're continuing to grow and are looking for motivated professionals who want to contribute to that growth while developing their own careers.

Our Hiring Process

We believe in a structured, consistent hiring process that gives candidates the opportunity to demonstrate their qualifications and abilities.

Apply Online: Submit your application and resume through Itechra's recruiting portal.
Application Review: Our sales leadership team reviews qualifications and relevant experience.
Pre-Employment Assessment: Selected candidates complete a 15-minute Criteria Cognitive Aptitude Test (CCAT) designed to evaluate problem-solving and learning ability. Assessment invitations are sent directly through Criteria Corp.
Interviews: Candidates selected to advance participate in interviews with our sales leadership team.

Assessment results are considered alongside relevant experience, qualifications, and interviews. No single assessment determines a hiring decision.

Reasonable accommodations are available throughout the application and hiring process. Applicants who require an accommodation may contact our People & Experience team at hr@itechra.com.

Ready to Prove What You Can Do?

If you're an experienced outbound sales professional who loves connecting with people, creating opportunities, and achieving measurable results, we'd love to hear from you.

Apply today and help drive Itechra's next chapter of growth!

This position is open to qualified candidates residing and working within the United States, subject to Itechra's ability to meet applicable state and local employment requirements.

Itechra, Inc. is an Equal Opportunity Employer. Employment decisions are made without regard to race, color, religion, sex, national origin, age, disability, veteran status, or any other characteristic protected by applicable federal, state, or local law.

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