Account Executive

Overview

You're the first full-time AE at Grow Surely, selling their AI-powered outbound appointment setting service to B2B companies making over $1M/year. You'll own the entire sales cycle—finding prospects, running demos, negotiating deals—while helping build the sales playbook from scratch alongside the founders.

Role Snapshot

Company Context

Stage: Bootstrapped/Early-stage (not venture-backed based on available info)

Size: 7 employees

Growth: At $1.5M ARR, hiring first AE signals they're ready to scale beyond founder-led sales

Market Position: Operating in a crowded outbound agency/service space—competing against hundreds of similar appointment-setting firms, but positioning around AI and their founder's track record (100+ clients helped)

GTM Reality

Pipeline Sources:

• 70-80% Outbound - You'll be doing most of your own prospecting via LinkedIn, email sequences, and potentially cold calling
• 20-30% Warm intros/referrals - Founder has network from previous clients, but these are inconsistent
• Minimal true inbound - Small company without major marketing engine

SDR/AE Structure: No SDR support initially—you're self-sourcing. Founder may help with warm intros and strategic accounts.

SE Support: No dedicated SE. You'll run all demos yourself and answer technical questions about their AI agents, Clay implementation, and data tools.

Competitive Landscape

Main Competitors: Other outbound agencies (SalesRoads, Martal Group), offshore SDR teams, in-house SDR builds, AI sales tools (Apollo, Clay with internal team)

How They Differentiate: AI-powered approach (using Clay, AI agents) vs traditional human-only outsourcing; founder credibility from helping 100+ companies; claim of "1-4 new B2B clients per month" results

Common Objections:

• "We tried outsourced SDRs before and it didn't work"
• "How is this different from hiring our own SDR?"
• "Your pricing seems high compared to offshore options"
• "How do I know your AI won't send spammy messages?"
• "We need to own our outbound process in-house"

Win Themes: Speed to results, no hiring/training headaches, founder expertise, technology edge over traditional agencies

What You'll Actually Do

Time Breakdown

Prospecting (40%) | Active Deals (35%) | Internal/Admin (25%)

Key Activities

• Prospecting: You're building your own pipeline. This means 1-2 hours daily on LinkedIn identifying B2B companies with $1M+ revenue (tech, SaaS, professional services), sending connection requests, engaging with posts, and running personalized outreach sequences. Expect 20-30 meaningful outreach touches per day.

• Discovery Calls: Running 5-10 discovery calls per week with VPs of Sales, founders, and revenue leaders. You're diagnosing their current outbound situation, understanding why past efforts failed, and qualifying if they have $3-10K/month budget and willingness to try an agency model.

• Demos: Showing their case studies, explaining the AI-powered process (Clay for data enrichment, AI agents for personalization), walking through example campaigns, and addressing the "how is this different" objection. Calls typically run 30-45 minutes.

• Proposal/Negotiation: Creating custom proposals (likely in Google Docs or basic tools), addressing procurement questions at larger companies, negotiating contract terms, and trying to close within 2-3 conversations after demo. Most deals will require at least one follow-up call and email thread.

• Internal Coordination: Weekly syncs with founders on deal strategy, feeding back market insights, helping shape positioning as you learn what resonates, potentially contributing to case studies and sales collateral that doesn't exist yet.

The Honest Reality

What's Hard

• You're building the plane while flying it: There's no established playbook, no battle cards, probably limited CRM hygiene. You'll be figuring out messaging, pricing objection handling, and qualification criteria through trial and error.

• Outbound service is a crowded, skeptical market: Most prospects have been burned by outsourced SDR agencies before. You'll hear "we tried this and it didn't work" constantly. Differentiating on AI/technology is hard when everyone claims AI now.

• Self-sourcing is a grind: No SDR feeding you meetings. You're doing 40% prospecting work yourself, which means less time selling. If you have a slow week of outreach, your pipeline suffers immediately.

• Small company growing pains: Limited resources, scrappy systems, you might be wearing multiple hats. If something breaks in the customer delivery or a client is unhappy, you might get pulled into firefighting.

• Founder-involved sales: The founder has been selling this successfully to 100+ clients. You need to prove you can replicate their success without their personal brand and network carrying the deal.

What Success Looks Like

• Closed $50-75K in new MRR per quarter (4-8 new clients at $3-10K/month)
• Built a repeatable prospecting system that generates 10-15 qualified conversations per week without founder intros
• 30-40% close rate on demos you run (realistic for consultative B2B service sale)
• Contributed to sales assets (deck, case studies, objection handling docs) that didn't exist before you joined

Who You're Selling To

Primary Buyers:

• VPs of Sales at $5-20M revenue B2B companies (often SaaS, tech services, agencies)
• Founders/CEOs at $1-5M revenue companies trying to build their first real sales function

What They Care About:

• Time to results: Can they see qualified meetings within 30 days, not 6 months of hiring/ramping an SDR?
• Quality over quantity: Are the meetings with actual buyers, not tire-kickers? Past agency experiences were high volume but low quality.
• Proof it works: Case studies, specific results (the "1-4 clients per month" claim), examples from their industry
• Not damaging their brand: Fear of spammy AI-generated messages ruining their reputation in a small market
• Cost vs hiring: Is $5-10K/month cheaper and less risky than a $70K+ SDR salary plus tools, training, management time?

Requirements

• 2-4 years B2B sales experience, preferably selling services/agencies or selling TO sales leaders (you need to understand their world)
• Proven self-sourcing ability: You've hit quota before while generating your own pipeline, not just working inbound leads
• Comfortable with ambiguity: Early-stage company, no formal training program, you'll be figuring things out and contributing to process
• Low ego, high learning speed: Founder says this explicitly—they need someone coachable who can iterate quickly based on what's working
• Willingness to grind: 40% of your time prospecting, lots of rejection, building from scratch isn't glamorous