Location: Toronto / Remote (North America)

Company Description

vSite by vGIS Inc. is the Operational Control Platform for Subsurface Infrastructure Projects. The system simplifies, de-risks, and streamlines projects by providing real-time insights powered by AI, AR, and 3D documentation. vSite enables teams to view instant answers, stay on schedule with AI-powered automation, and collaborate seamlessly between owners, engineers, locators, and contractors.

The Role

As Executive Assistant to the CEO, you’ll work directly alongside Alec Pestov to drive growth across vSite’s target markets: utility contractors and municipal owners across North America. This isn’t a traditional EA role. You’ll own outbound prospecting, keep the sales pipeline moving, and make sure the CEO’s time is focused on the highest-value conversations.

This isn’t about managing calendars. It’s about understanding the operational pain points that cost contractors real money — late cost coding, double-entry into payroll systems, lost packing slips, delayed pay apps — and making sure the right people hear about vSite at the right time.

Key Responsibilities

Outbound Prospecting

• Execute multi-channel outreach campaigns (cold calling, email, LinkedIn) targeting utility contractors and municipal engineering departments
• Research target accounts using bidding databases, LinkedIn, trade association directories, and municipal procurement records
• Make 50+ strategic outreach touches daily across phone, email, and social channels
• Identify and connect with key decision-makers: VPs of operations, project directors, public works directors, construction services managers

Pipeline & CEO Support

• Own CRM hygiene — every prospect, conversation, and follow-up accurately logged so nothing falls through
• Monitor the pipeline and flag deals that have gone cold, meetings that need scheduling, or proposals that need follow-up
• Prepare the CEO for calls and demos — briefing notes, background research, talking points
• Draft follow-up communications on the CEO’s behalf after meetings, demos, and events

Lead Qualification & Discovery

• Conduct discovery calls to uncover operational pain points around field data capture, production tracking, and documentation workflows
• Qualify prospects based on project portfolio size ($1M–$50M projects), geographic fit, and operational maturity
• Assess readiness for change and budget authority before booking with the CEO
• Document prospect intelligence in CRM with detailed notes on pain points, current tools, and decision-making process

Market Intelligence

• Track competitor positioning and identify differentiation opportunities
• Monitor construction industry news, infrastructure funding announcements, and regional market trends
• Share field feedback with product and marketing teams to refine positioning and messaging

Event & Association Activation

• Support trade show and event follow-up (ORBA, regional construction conferences)
• Coordinate outreach to association contacts and industry network connections
• Manage inbound interest from events — triage, respond, and route with speed and professionalism

What We’re Looking For

Required:

• 1+ years in an EA, SDR/BDR, inside sales, or customer-facing role
• Proven ability to hit activity targets and take ownership without being managed
• Strong phone presence — confident, consultative, and professional on cold calls
• Excellent written communication for email campaigns and LinkedIn outreach
• Highly organized — you track details others miss and nothing slips through
• Comfortable with CRM systems and sales engagement tools

Highly Valued (Not Required):

• Construction industry knowledge or experience (contracting, field operations, estimating, project management)
• B2B SaaS sales or sales support experience in vertical-specific software
• Experience coordinating for a founder or CEO in a growth-stage company
• Familiarity with utility construction workflows, ERP systems, or project management software
• Experience with government/municipal buyers or public procurement processes

Personal Attributes:

• Ownership mentality: If it lands in your court, it gets done — no follow-up required
• Curiosity: You ask great questions and genuinely want to understand how contractors run their businesses
• Coachability: You actively seek feedback, iterate, and improve continuously
• Grit: You handle rejection well and stay motivated when prospects say no
• Proactive: You see what needs to happen before being told
• Entrepreneurial: You’re excited about ground-floor opportunities where your work directly drives growth