Sales Representative

Overview

You sell digital marketing services for a 21-person agency. You're reaching out to small business owners and marketing managers, trying to get them to sign monthly retainers for services like SEO, paid ads, social media management, or website work. You're handling most of the sales cycle yourself—prospecting, qualifying, presenting proposals, and closing.

Role Snapshot

Company Context

Stage: Bootstrapped/Established small agency

Size: 21 employees

Growth: Unknown, but actively hiring sales roles

Market Position: One of thousands of digital marketing agencies competing for SMB budgets in a crowded, commoditized market

GTM Reality

Pipeline Sources:

• 80% Outbound - Cold calling, LinkedIn outreach, email campaigns to business owners
• 15% Referrals - Existing clients or personal network
• 5% Inbound - Website inquiries, but likely minimal brand awareness

SDR/AE Structure: Self-source everything. No SDR team.

SE Support: No dedicated technical support. You present the work, possibly with help from the CEO or a senior account manager on bigger deals.

Competitive Landscape

Main Competitors: Hundreds of other digital marketing agencies, freelancers, in-house teams, and DIY tools (HubSpot, Mailchimp, etc.)

How They Differentiate: Unclear without more info—likely relationships, case studies, or specific vertical expertise

Common Objections: "We tried this before and it didn't work," "Too expensive," "We're doing it in-house," "How do I know you'll get results?"

Win Themes: Trust-building, showing concrete ROI examples, being more responsive than competitors, offering bundled services

What You'll Actually Do

Time Breakdown

Prospecting (50%) | Active Deals (30%) | Admin/Internal (20%)

Key Activities

• Cold outreach: Making 40-60 calls per day or sending 50+ personalized LinkedIn/email messages to small business owners. Most don't respond. You're trying to book 5-10 discovery calls per week.
• Discovery and needs assessment: Getting on the phone with prospects to understand their marketing pain points, current efforts, and budget. You're qualifying whether they can afford $2-10K/month and if they're actually serious.
• Proposal creation: Building custom proposals (likely using templates) that outline services, timelines, and pricing. You're sending 3-5 proposals per week, and most go nowhere or ghost after "we'll think about it."
• Follow-up and closing: Chasing prospects via email, phone, and LinkedIn to get decisions. You're dealing with slow responses, budget approval delays, and competing priorities on their end.

The Honest Reality

What's Hard

• Rejection and ghosting: Most prospects don't respond or aren't interested. Of those who take calls, many ghost after the proposal stage. You need thick skin.
• Price sensitivity: SMBs are watching every dollar. You'll hear "that's too expensive" constantly, even when your pricing is competitive. Closing often requires discounting or payment plans.
• Commoditized market: Digital marketing services are everywhere. It's hard to differentiate, and prospects often choose based on the cheapest option or whoever follows up most persistently.
• Inconsistent commission: If this is heavily commission-based, your income will fluctuate month to month depending on closes. Early months may be lean while you build pipeline.
• Wearing multiple hats: At a 21-person shop, you might be expected to help with client onboarding, reporting, or even project management post-sale.

What Success Looks Like

• Closing 3-5 new clients per month at an average retainer of $5K/month
• Building a referral engine where happy clients bring in warm leads
• Consistently hitting activity metrics (calls made, meetings booked, proposals sent)

Who You're Selling To

Primary Buyers:

• Small business owners (restaurants, local services, retail)
• Marketing managers or directors at mid-sized companies (50-200 employees)

What They Care About:

• ROI: They need to see how marketing spend translates to leads, sales, or brand awareness
• Trust: They've been burned before by agencies that overpromised and underdelivered
• Simplicity: They don't want to manage five vendors—they want one agency that handles everything
• Responsiveness: They want someone who answers their calls and emails quickly

Requirements

• 1-2 years of sales experience (B2B or agency sales preferred, but entry-level may be considered)
• Comfortable with high-volume outbound prospecting (cold calling, email, LinkedIn)
• Ability to handle rejection and stay motivated through long sales cycles
• Basic understanding of digital marketing concepts (SEO, PPC, social media)
• Self-starter mentality—this isn't a structured sales org with heavy enablement
• Willing to work on a commission-heavy comp plan (base may be low or nonexistent)