Sales Operations / SDR Team Lead

Overview

You're building the operational foundation for Zorro's outbound SDR team while actively coaching junior reps. You'll own CRM processes, lead routing, and reporting dashboards, then spend the rest of your time listening to SDR calls, refining messaging, and helping reps book more meetings with benefits brokers and HR leaders. This is a player-coach role—you're not purely on the tools, but you're not a full manager either.

Role Snapshot

Company Context

Stage: Likely Series A/B based on 95 employees and multi-year hypergrowth

Size: 95 employees

Growth: "Growing several multiples year after year" per VP Sales—they're scaling fast and need process to catch up

Market Position: ICHRA is a newer benefits model (post-2020 IRS rules), so they're in education/category creation mode against traditional group health plans

GTM Reality

Pipeline Sources:

• 70%+ Outbound - SDRs calling/emailing benefits brokers and HR leaders at SMBs/mid-market companies. ICHRA requires explanation, so most deals start with cold outreach.
• 20% Partner/Broker referrals - Brokers who already know ICHRA send clients their way
• 10% Inbound - Some website traffic from employers Googling ICHRA alternatives, but this is early-stage awareness

SDR/AE Structure: You're managing the SDR team (likely 3-6 reps based on company size). They book meetings, AEs close them. Classic two-tier model.

SE Support: Likely light—ICHRA is administratively complex but not deeply technical. AEs probably handle most demos solo.

Competitive Landscape

Main Competitors: Other ICHRA platforms (Take Command Health, Thatch, Remodel Health), traditional PEOs, and the status quo (sticking with group health plans)

How They Differentiate: "Tech-forward + people-centric"—they're positioning as more automated/modern than legacy benefits admins, but with better service than pure self-serve platforms

Common Objections:

• "Our employees don't want to shop for their own insurance"
• "ICHRA sounds complicated—what if they screw it up?"
• "Our broker says group plans are simpler"

Win Themes: Cost savings for employers, more choice for employees, works well for distributed/remote teams where group plans are a nightmare

What You'll Actually Do

Time Breakdown

SDR Coaching (35%) | Ops/Systems Work (40%) | Meetings/Reporting (25%)

Key Activities

• CRM Cleanup & Process Design: You're in Salesforce or HubSpot daily—fixing duplicate records, building lead routing rules, creating dashboards for Jeff to review SDR activity. The SDRs are probably logging stuff inconsistently, so you're the enforcement layer.

• Call Coaching & Messaging Refinement: You listen to 5-10 SDR calls per week, give feedback in 1:1s, and tweak cold call scripts. ICHRA is confusing to explain, so a lot of your job is helping reps get better at the first 30 seconds of a cold call.

• Territory & List Management: You figure out which SDRs call which accounts (by geography, company size, or broker relationship). You also pull lists, check data quality, and make sure reps aren't burning through bad contacts.

• Reporting & Forecasting: You build weekly reports for Jeff: dials, connects, meetings booked, show rates, conversion to SQL. You're the person who knows if the team is on track or falling behind.

• Onboarding New SDRs: When Zorro hires a new SDR, you're probably running their first two weeks—teaching them the pitch, the CRM, and how to handle objections.

The Honest Reality

What's Hard

• Ops work is tedious: CRM hygiene, data cleanup, building reports—it's not glamorous. You're fixing messes more than building shiny new systems.

• You're not the manager, but you're also not a peer: The SDRs report to Jeff, not you. So you're coaching them without having formal authority. If someone ignores your feedback, you escalate to Jeff, which can be awkward.

• ICHRA is a tough sell for SDRs: It's a new concept, so prospects hang up a lot. You'll spend time motivating reps through rejection and refining messaging that doesn't land.

• You're building the plane while flying it: Zorro is scaling fast, so processes are probably half-baked. You're documenting stuff that doesn't exist yet, which means a lot of "figure it out as you go."

What Success Looks Like

• SDR meeting quota goes from 60% attainment to 85%+ because your coaching and process improvements work
• You cut the time Jeff spends in Salesforce by 50% because your dashboards give him what he needs at a glance
• New SDR ramp time drops from 8 weeks to 4 weeks because you built a real onboarding playbook

Who You're Selling To

Primary Buyers (that SDRs are booking meetings with):

• Benefits brokers (they recommend ICHRA to their clients)
• HR Directors / Benefits Managers at 50-500 person companies
• CFOs at cost-conscious SMBs looking to cut health insurance spend

What They Care About:

• Cost predictability: ICHRA lets employers set a fixed reimbursement budget vs. unpredictable group plan renewals
• Compliance risk: They're terrified of screwing up ACA/ERISA rules—Zorro needs to feel like a safe pair of hands
• Employee experience: If employees hate shopping for plans, they'll hear about it. Zorro's concierge support is a key selling point.

Requirements

• 1-2 years in sales (probably crushed quota as an SDR or BDR)
• Comfortable in a CRM (Salesforce or HubSpot)—you'll live there
• You like coaching people and don't mind repetitive process work
• Bonus: Some exposure to benefits/insurance (but not required—you'll learn ICHRA fast)
• Willingness to sit in Boston preferred (easier to coach SDRs in person), but remote is possible
• Scrappy/self-starter mindset—you won't have a 50-page playbook to follow