Sales Development Representative

Overview

You're the first line of outreach for Bolto, targeting HR leaders at funded startups to book qualified demos. Your day is cold calls, emails, LinkedIn messages, and fighting through gatekeepers to get 15 minutes with someone who manages recruiting, payroll, or HR ops. You're looking for companies that just raised funding, are hiring aggressively, or are complaining about their current tools. Most people you contact won't respond or won't be ready to buy.

Role Snapshot

Company Context

Stage: YC-backed seed stage (15 employees)

Size: 15 people total

Growth: Recently doubled headcount, building out go-to-market team

Market Position: New entrant fighting for attention in a space dominated by Rippling, Gusto, Greenhouse, and BambooHR

GTM Reality

Pipeline Sources:

• 90% Your outbound activity - lists of funded startups, YC companies, LinkedIn searches for HR titles
• 10% Inbound follow-up - website form fills that didn't book a time, demo requests

SDR/AE Structure: You book, AEs close (likely 1-2 AEs initially)

SE Support: N/A for your role

Competitive Landscape

Main Competitors: Rippling, Deel, Gusto, Greenhouse + BambooHR combos

How They Differentiate: All-in-one platform built from ground up (not stitched together acquisitions), AI for compliance automation, better UX

Common Objections: "We're happy with Gusto", "Not looking to switch right now", "Send me info" (brush-off), "Too small/unproven"

Win Themes: Consolidation saves time and money, AI actually useful for tedious compliance work, faster to implement than Rippling

What You'll Actually Do

Time Breakdown

Cold Calling (40%) | Email/LinkedIn (30%) | Research/List Building (20%) | Meetings (10%)

Key Activities

• Cold Calling: Dial 60-80 numbers per day to reach HR leaders, People Ops managers, or founders at 20-200 person startups. Most calls go to voicemail. When you get someone live, you have 30 seconds to explain why Bolto is worth 15 minutes of their time before they hang up or say "send me info."
• Email Sequences: Send 80-100 emails per day using Outreach or Salesloft. Personalize the first line with something about their company (recent funding, job postings, LinkedIn post). Most get ignored. You're thrilled with a 2-3% response rate.
• LinkedIn Outreach: Send connection requests and messages to HR leaders. Most don't accept or respond. When they do, it's often "not interested right now" or "can you send info?" which rarely goes anywhere.
• List Building: Spend 1-2 hours daily building targeted lists. Use Crunchbase for recently funded companies, LinkedIn for HR leaders at fast-growing startups, YC directories for batch mates. Quality of your list determines your response rates.
• Discovery/Handoff: When someone agrees to a meeting, you run a quick 10-15 min qualifying call. Do they have budget? Are they actually unhappy with current tools? Is there a timeline? If yes to all three, you hand them to an AE. If not, you nurture or disqualify.

The Honest Reality

What's Hard

• Rejection is constant: 95%+ of your outreach gets ignored or rejected. You'll hear "not interested" 20+ times a day. If you take it personally, you'll burn out.
• Gatekeepers: Getting past executive assistants or HR coordinators to reach the actual decision maker is a daily battle. "They're in meetings all day" becomes your least favorite phrase.
• Switching inertia: Even companies that hate their current tools often aren't ready to deal with migration pain. You'll have great conversations that go nowhere because "now isn't the right time."
• Early-stage stigma: Some prospects won't take a meeting because you're 15 people. They assume you're not ready for primetime or will get acquired/shut down.
• Repetitive grind: You'll say the same pitch 50 times a day. It gets monotonous. The challenge is staying sharp and enthusiastic on call #60.

What Success Looks Like

• Booking 12-15 qualified meetings per month (meetings that show up and fit ICP)
• 20-25% of your booked meetings convert to pipeline (AE moves them to discovery/demo stage)
• Maintaining 60+ calls and 80+ emails per day consistently
• Building a territory knowledge—knowing which companies just raised rounds, are hiring aggressively, or posted about HR pain on social

Who You're Selling To

Primary Targets:

• Head of People / VP People at 30-150 person startups
• People Operations Managers at Series A-C companies
• Founders / COOs at <50 person companies (they're often wearing the HR hat)

What They Care About:

• Reducing time spent on admin work (they're drowning in recruiting, payroll, compliance tasks)
• Tool consolidation (tired of logging into 5 different systems)
• Scaling HR ops without adding headcount
• Compliance confidence (especially if they're hiring in multiple states or going global)

Requirements

• 0-2 years of SDR/BDR experience (or this is your first SDR role out of college)
• High tolerance for rejection and ability to stay motivated through slumps
• Comfortable making 60-80 cold calls per day
• Coachable—you'll need to iterate on messaging and learn what resonates
• Self-starter mentality—at a 15-person company, there's no formal training program or SDR playbook yet
• Genuine curiosity about startups and HR tech (you'll be talking to HR leaders all day—helps if you find the space interesting)