Evan Cassidy

Sales Development Representative

Decagon

SDRBalancedTransactional
Posted by Evan Cassidy

Overview

You identify and qualify companies that could benefit from AI-powered customer support, then book discovery meetings for Account Executives. You work inbound leads (demo requests, G2 traffic, content downloads) and run outbound sequences to target accounts. You're talking to VP/Director of Customer Experience, Head of Support, or Customer Success leaders.


Role Snapshot

AspectDetails
Role TypeInbound/Outbound SDR
Sales MotionBalanced - roughly 50/50 inbound qualification and outbound prospecting
Deal ComplexityN/A (you're not closing deals, you're booking meetings)
Sales CycleN/A
Deal SizeN/A
Quota (est.)12-15 qualified meetings per month

Company Context

Stage: Series D ($4.5B valuation, $250M raised Feb 2025)

Size: 301 employees

Growth: Hyper-growth - massive hiring velocity on GTM team. VP Sales posted they went from 10 to 301 people in 18 months. You're joining a rocketship.

Market Position: Category leader with strong inbound demand (4.9 stars on G2, Deutsche Telekom as reference customer). But still early enough that you're not just order-taking.


GTM Reality

Pipeline Sources:

  • 50% Inbound - Demo requests, G2 traffic, content downloads, webinar signups. These are warmer but not all qualified. You need to separate tire-kickers from real buyers.
  • 50% Outbound - You get target account lists (companies with 200+ support agents, high-growth SaaS, ecommerce, fintech) and run sequences (cold calls, emails, LinkedIn). You're building lists and testing messaging.

SDR/AE Structure: You feed meetings to 3-4 AEs. Each SDR has their own book of target accounts plus a queue of inbound leads to work.

Coaching/Enablement: Weekly 1:1s with SDR manager, call reviews, monthly training on messaging/objection handling. They're investing in ramping people fast.


Competitive Landscape

Main Competitors: Intercom Fin, Sierra AI, Ada, Forethought, Ultimate.ai, Zendesk AI

Your Job in Competitive Deals: You need to figure out what they're using now and why they're looking. Are they unhappy with current chatbot? Evaluating multiple vendors? Just exploring AI? You qualify on budget, authority, need, timeline (BANT).

Common Objections You'll Hear:

  • "We already have Zendesk/Intercom" - your response: "Are you using their AI features? How's that going?"
  • "Just exploring, not ready to buy" - you need to find pain and urgency
  • "Send me info" - the classic brush-off, you need to get a meeting instead

What You'll Actually Do

Time Breakdown

Outbound Prospecting (40%) | Inbound Lead Qualification (40%) | Admin/Internal (20%)

Key Activities

  • Inbound Lead Qualification: You get 8-12 inbound leads per week (demo requests, G2 traffic). You call/email within 5 minutes. Half are junk (students, competitors, wrong fit). You're figuring out: Do they have a support team of 50+ agents? Is there a project or pain? Who's the decision maker? Can you get them on a 15-min call to qualify, then book a full AE meeting?

  • Cold Calling: You make 40-50 dials per day to target accounts. You're calling VP Customer Experience, Director of Support, Head of Customer Success. Most don't pick up. You leave voicemails, send follow-up emails. You're trying to get 2-3 conversations per day that turn into meetings.

  • Email Sequences: You build and run Outreach/Salesloft sequences (5-7 touch cadence over 2 weeks). You're A/B testing subject lines, pain points, case studies. You personalize the first email with something specific ("Saw you're hiring 10 support reps, guessing volume is growing fast...").

  • Discovery/Qualification Calls: When someone responds, you get them on a 10-15 min call. You're asking: What's your current support setup? How many agents? What tools? What's working/not working? Is there a project or initiative around AI? Who else is involved? You're qualifying to make sure it's worth an AE's time, then you book a 30-min discovery meeting.

  • LinkedIn/Social Prospecting: You send InMails, engage with posts, look for warm intro paths. Some accounts are locked down and email/phone don't work - you need creative ways in.

  • CRM Hygiene: You log every call, email, outcome in Salesforce. You update lead status, book meetings, write detailed notes so AEs know what was discussed. This takes 30-45 min per day.


The Honest Reality

What's Hard

  • Rejection is constant: 90% of your cold calls go to voicemail. Half your emails get ignored. You get a lot of "not interested" and "just send me info" brush-offs. You need thick skin.

  • Inbound quality varies: Not every demo request is a real opportunity. You waste time on students doing research, competitors snooping, or people at tiny companies with no budget. You need to disqualify fast.

  • Gatekeepers and org charts: Getting to the VP of CX at a 2,000-person company is hard. EAs screen calls. You're trying LinkedIn, email, calling other departments to find a way in.

  • Quota pressure: You need 3 qualified meetings per week, every week. If you have a bad week, you're behind and stressed. The job is repetitive - you're saying the same pitch 50 times a day.

What Success Looks Like

  • Hitting 12-15 qualified meetings per month consistently
  • 50%+ of your meetings convert to "sales accepted opportunities" (AE agrees it's legit)
  • High activity (200+ dials/week, 100+ emails, 10+ LinkedIn touches)
  • Getting promoted to AE in 12-18 months if you crush it

Who You're Selling To

Primary Personas:

  • VP/Director of Customer Experience or Customer Support (budget owner)
  • Head of Customer Success (at some companies)
  • Operations leaders responsible for support efficiency

What They Care About:

  • Do you understand my pain? They're drowning in ticket volume, hiring is expensive, CSAT is slipping. If you lead with generic AI hype, they'll blow you off.
  • Is this worth my time? They get 10 vendor pitches per week. You need a sharp hook - a case study, a specific pain point, a warm intro.
  • Fast/easy to evaluate? They don't want a 6-month sales cycle. If you can show fast ROI and easy implementation, they'll take a meeting.

Requirements

  • 0-2 years experience (this is entry-level, but prior SDR experience helps)
  • Comfortable making 50+ cold calls per day and hearing "no" constantly
  • Coachable - you'll get a lot of feedback on your pitch, email copy, call technique
  • Organized - you're juggling 50+ active leads/accounts, you need systems
  • Competitive and metrics-driven - you're measured on activity and meetings booked
  • Bonus: Interest in AI/tech, prior experience in customer support or SaaS