Chase Simmonds

BDR (Business Development Representative)

Rollstack

BDROutbound HeavyConsultativeRemote📍 Remote
Deal Size: $20-80K ACV
Posted by Chase Simmonds

Overview

You're the first or second BDR at Rollstack, a 32-person company that automates data-driven reporting. You'll spend your day cold calling and emailing VPs of Analytics, BI Directors, and data team leads at mid-market to enterprise companies, trying to explain why they should stop manually updating slide decks with chart screenshots and use Rollstack instead.


Role Snapshot

AspectDetails
Role TypeOutbound BDR - pure prospecting, no deal ownership
Sales MotionOutbound-heavy (80-90%) - building pipeline from scratch
Deal ComplexityConsultative - not obvious pain point, requires education
Sales CycleN/A for BDR - you book meetings, AEs close (likely 2-4 months)
Deal SizeLikely $20-80K ACV based on enterprise BI tool pricing
Quota (est.)15-20 qualified meetings/month, 8-12 SAOs/month

Company Context

Stage: Early (likely Seed/Series A based on 32 employees, backed by Insight Partners)

Size: 32 employees - small team, you'll know everyone

Growth: Hiring first/second BDR suggests they're ready to scale outbound motion

Market Position: Category creator/educator - "reporting automation" isn't a mature category yet. Most prospects solve this with manual work or homegrown scripts.


GTM Reality

Pipeline Sources:

  • 10-20% Inbound - small flow from website, content, maybe some PLG interest from folks who found them
  • 80-90% Outbound - cold calling, LinkedIn, email sequences to target accounts
  • Partners are likely minimal at this stage

SDR/AE Structure: You're building the BDR function. Likely 1-2 AEs you'll feed meetings to. Expect to be part of defining the process, not following a well-oiled machine.

SE Support: Probably shared or part-time SE support for technical deep dives, but you won't need them for initial meetings.


Competitive Landscape

Main Competitors: Hard to identify direct competitors because category is emerging. You'll compete against:

  • Status quo (manual reporting work)
  • Homegrown automation scripts
  • Presentation automation tools
  • BI platforms' native scheduling features

How They Differentiate: Direct integration with Tableau/Looker/Power BI, AI-powered insights, automated content generation vs manual copy-paste or basic scheduling.

Common Objections:

  • "We already have our process" (manual updates, assistants, junior analysts)
  • "Our BI tool already does scheduling" (doesn't do rich slide decks)
  • "We don't make that many reports" (until you show them they make 50+ recurring reports)
  • "That's not a priority right now" (not obvious pain)

Win Themes: Time savings for data teams, consistency in reporting, scalability when report volume grows.


What You'll Actually Do

Time Breakdown

Cold Calling (35%) | Email/LinkedIn (30%) | Research (20%) | Meetings/Admin (15%)

Key Activities

  • Cold Calling: 50-70 calls per day to VPs of Analytics, BI Directors, Data Platform leads. You're calling into companies using Tableau/Looker/Power BI (you can see this from job postings, tech stacks, LinkedIn). Most don't answer. Many who do aren't interested.

  • Email Sequences: Writing and sending personalized emails explaining the reporting automation use case. You're trying to get 30 seconds of attention to explain a problem they might not know they have. Response rates will be low (2-5%).

  • Account Research: Figuring out which companies have big enough data teams to need this, who owns reporting, finding phone numbers and email addresses. You'll spend time on LinkedIn, ZoomInfo, company websites trying to identify the right person.

  • Discovery Meetings: When you get someone on the phone or in a meeting, you're qualifying whether they have recurring reporting needs (board decks, executive updates, client reports), what tools they use, how many reports they create, and whether they have budget/authority to buy a new tool.


The Honest Reality

What's Hard

  • You're educating a market - most prospects don't wake up thinking "I need reporting automation." You're creating demand, not capturing it. Expect a lot of "interesting but not now."

  • Cold calling into data teams is rough - these people are heads-down technical folks who don't love sales calls. Connect rates will be low. You'll hear a lot of "just send me an email."

  • Early-stage means less structure - there's no proven playbook yet. You'll be testing messaging, ICPs, and qualification criteria. What works one week might not work the next. You need to be comfortable with ambiguity.

  • Long feedback loops - even when you book meetings, you won't see most of them close for months. Hard to know if you're booking good pipeline or wasting AE time.

What Success Looks Like

  • Hit your meeting quota consistently - 15-20 qualified meetings per month, 8-12 that turn into real sales opportunities
  • High meeting-to-SAO conversion - AEs actually want the meetings you book (60%+ should become pipeline)
  • You identify the ICP - figure out which company sizes, industries, and buyer titles actually convert

Who You're Selling To

Primary Buyers:

  • VP/Director of Analytics - owns the reporting function, feels the pain of report requests
  • Head of Business Intelligence - technical owner of BI tools
  • Chief Data Officer - strategic buyer at larger orgs

What They Care About:

  • Time savings for their team - analysts spending hours updating decks instead of doing analysis
  • Scalability - report requests growing faster than headcount
  • Consistency and quality - manual updates lead to errors, outdated data, formatting issues
  • They're skeptical of new tools - already have a BI platform, don't want another thing to manage

Requirements

  • 1-2 years in SDR/BDR role - or strong internship/entry sales experience with proven cold calling ability
  • Comfortable with ambiguity - no mature playbook here, you'll be figuring things out
  • Can explain technical concepts simply - talking to data people about their workflow without getting too deep in the weeds
  • High activity tolerance - making 50+ calls/day, sending 100+ emails, comfortable with rejection
  • Self-directed - small team means less hand-holding, you need to manage your own time and activity