PlanITROI is hiring an Executive Sales Assistant to the CEO to work directly with our CEO, and our Chief Strategy Officer. This person will help drive outbound sales activity, activate executive relationships, follow up on qualified leads, and make sure new business appointments are scheduled every week.

The right person is proactive, organized, persistent, professional, and comfortable communicating with U.S executives, business owners, referral partners, and prospects. You must be able to research the right people, send clear emails, make professional calls, use LinkedIn effectively, manage follow-up, and keep Salesforce current.

This role is not for someone looking for basic administrative work. It is for someone who understands sales, relationships, urgency, research, CRM discipline, and follow-through.

About PlanITROI

At PlanITROI, we believe technology should create opportunities, not waste. Through industry-leading IT Asset Disposition (ITAD), refurbishment, repair, redeployment, and resale services, we help organizations maximize the value of their technology investments while extending device lifecycles and making affordable technology accessible to schools, families, nonprofits, businesses, and communities around the world.

Our mission is simple: Change Lives with Affordable Technology while helping organizations maximize the value of their retired IT assets.

As we continue to grow, we are investing in relationship-driven sales, executive outreach, strategic partnerships, and new customer acquisition.

Role Overview

You will support the CEO and CSO by helping turn relationships, introductions, qualified leads, and targeted prospects into scheduled appointments and active business opportunities.

You will use Apollo.io, Salesforce, LinkedIn, email, phone calls, and AI-enabled tools to research prospects, identify and engage B2B contacts, manage outreach, document activity, and complete follow-up.

You will work with:

The PlanITROI key contacts within their professional network. Executives, owners, decision-makers, referral partners, B2B strategic contacts. Warm introductions and existing relationships. Qualified leads from the lead generation team. Target accounts identified through research and outbound sales campaigns.

Your responsibility is to keep opportunities moving from outreach to appointment, from meeting to next step, and from next step to signed agreement or proper handoff to the Client Success Team.

Engagement Type: Remote - Contractor

Location: Latin American countries within the Eastern Standard Time (EST).

Key Responsibilities

• Work directly with the CEO and CSO to organize, prioritize, and execute outbound sales outreach.
• Research companies, decision-makers, executives, referral sources, and relationship paths.
• Keep all active prospects, B2B contacts and accounts, and follow-up items organized and current.
• Use Apollo.io to identify, enrich, organize, and prioritize leads.
• Use Salesforce to track every call, email, LinkedIn touch, task, note, meeting outcome, and follow-up.
• Send polished, personalized outbound emails.
• Make professional calls to schedule appointments and advance conversations.
• Use LinkedIn for prospect research, direct outreach, engagement, and thought leadership support.
• Follow up on PlanITROI’s executive network, warm relationships, referrals, inbound leads, and lead generation team leads.
• Coordinate meeting scheduling, confirmations, reminders, and next-step communication.
• Take meeting notes when needed and follow through until next steps are completed.
• Prepare prospect briefs, account research, call summaries, and meeting notes.
• Track opportunities through appointment setting, post-meeting follow-up, proposal support, contract progress, and handoff to Client Success.
• Partner with sales, marketing, lead generation, and Client Success to keep opportunities moving.
• Maintain confidentiality and professionalism with executive relationships and strategic opportunities.
• This role requires travel to the United States.
• Must have a reliable, high-speed internet connection suitable for video calls, CRM work, and real-time communication

What Success Looks Like

Success in this role is simple and measurable:

• 5-10 Qualified new business appointments are scheduled every week.
• PlanITROI’s executive network is researched, organized, contacted, and followed up on.
• Qualified leads receive fast, professional follow-up.
• Salesforce is accurate, current, and complete.
• Every prospect has a clear next step.
• Post-meeting follow-up happens quickly.
• No qualified lead, relationship, or opportunity falls through the cracks.

Qualifications

• 3–5+ years of experience in outbound sales support, appointment setting, lead follow-up, business development, sales research, executive outreach, B2B contact management, or executive sales assistance.
• Strong experience with email, phone, LinkedIn, and CRM-based follow-up.
• Experience using Apollo.io or similar prospecting tools for research, contact identification, lead enrichment, and list building.
• Strong Salesforce proficiency, including activity logging, task management, account updates, contact updates, notes, and follow-up tracking.
• Excellent written and verbal English communication skills with the ability to communicate professionally with U.S. and Global executives.
• Strong business writing skills with the ability to write clear, concise, personalized emails.
• Professional phone presence and confidence calling executives, decision-makers, referral partners, and prospects.
• Strong research skills and ability to quickly understand companies, contacts, industries, and business opportunities.
• Expert experience using LinkedIn for sales outreach, research, direct communication, and relationship development.
• Strong organization, attention to detail, ownership, and follow-through.
• Experience working directly with Executives, founders, business owners, executives, or senior sales leaders preferred.
• Proficiency in Microsoft Office, and related productivity tools.
• Familiarity with AI tools for research, writing, prospecting, and workflow efficiency preferred.

The Right Person

• Does not wait to be told what to do.
• Knows how to move sales opportunities and B2B relationships forward.
• Communicates with polish, professionalism, and urgency.
• Is comfortable representing the CEO and CSO externally.
• Understands how to communicate with U.S. and Global executives in English.
• Is confident using Apollo.io, Salesforce, LinkedIn, email, and phone.
• Is disciplined with notes, tasks, CRM updates, and follow-up.
• Is persistent without being pushy.
• Understands that the job is not finished when the meeting is booked.
• Takes ownership until the next step is completed.

This Role Is Not for Someone Who

• Wants a passive administrative assistant role.
• Avoids outbound sales activity.
• Is uncomfortable making phone calls.
• Struggles with written or spoken executive-level English.
• Waits to be told every next step.
• Does not keep Salesforce updated.
• Is disorganized with notes, tasks, and follow-up.
• Cannot manage multiple prospects and conversations at once.
• Is uncomfortable representing senior leadership.
• Thinks the work ends once a meeting is scheduled.

Why Join PlanITROI?

You will work directly with professional direct and very accountable CEO and Chief Strategy Officer on business development that matters. While your friends, family and significant others have a job that pays the bills, you will be helping PlanITROI create new relationships, expand its sales pipeline, grow strategic accounts, and advance our mission of Changing Lives with Affordable Technology.