Sales Manager

Overview

You're managing a team of 5-8 AEs (likely mid-market or enterprise-focused) selling Remote's global HR and payroll platform. Your day is split between coaching reps on active deals, running forecast calls, and hiring to grow the team. You're not carrying an individual quota, but you own the team's number - likely $4-8M in annual bookings depending on team size and segment.

Role Snapshot

Company Context

Stage: Late-stage private (14,589 employees)

Size: ~14,600 employees globally

Growth: New CBO hire signals GTM expansion - you're likely hiring aggressively

Market Position: Established player in crowded global employment space

GTM Reality

Pipeline Sources (for your team):

• Mix of inbound leads from marketing and outbound prospecting by SDRs
• Reps work 15-25 active opportunities at a time, juggling different cycle stages

SDR/AE Structure: Your AEs get leads from SDRs and also self-source some pipeline

SE Support: Limited - reps lean on internal compliance/country specialists for complex deals

Competitive Landscape

Main Competitors: Deel, Rippling, Oyster, traditional PEOs

How They Differentiate: Compliance rigor, infrastructure depth, enterprise-grade reliability

Common Objections: Price (competitors undercut), incumbent switching costs, "we'll handle it ourselves"

Your Job: Coach reps on navigating procurement, handling price objections, and building multi-threading strategies to get deals unstuck

What You'll Actually Do

Time Breakdown

Deal Coaching/Pipeline Reviews (35%) | Forecasting/Leadership Meetings (25%) | Hiring/Onboarding (20%) | 1-on-1s/Team Development (20%)

Key Activities

• Deal coaching: You're joining late-stage calls to help reps navigate legal reviews, handle pricing objections, or close a champion. Reps pull you in when deals stall or they need executive presence. You're listening to call recordings and giving feedback on discovery, demos, and objection handling.
• Pipeline and forecast reviews: You run weekly pipeline reviews with your team - scrubbing deals, stress-testing commit forecast, pushing reps to move deals forward or disqualify losers. You roll up a forecast to your VP and defend it every week.
• Hiring: You're recruiting to grow the team or backfill attrition. Screening resumes, running interviews, selling candidates on Remote. If the CBO is ramping GTM, you might hire 2-4 people this year.
• 1-on-1s and performance management: Weekly 1-on-1s with each rep - reviewing their numbers, coaching on deals, addressing blockers. You're managing underperformers (PIPs, coaching plans) and developing high performers for promotion.
• Cross-functional coordination: You're in Slack with marketing (lead quality issues), sales ops (comp plan questions, territory changes), and product (customer feedback). Lots of internal meetings.

The Honest Reality

What's Hard

• You own the number but don't control the deals: Reps miss quota, deals slip, and it's your forecast that's wrong. You're accountable for team performance but can't personally close every deal.
• Pipeline coverage is constant stress: You need 3-4x pipeline coverage to hit the number. If pipeline dips, you're scrambling - pushing reps to prospect more, asking SDRs for more leads, running "pipeline generation sprints."
• Managing underperformers: You inherit reps who aren't cutting it. You're putting them on coaching plans, delivering hard feedback, and sometimes managing them out. It's uncomfortable and time-consuming.
• Forecast pressure: You commit a number to leadership every week. If your team misses, you're explaining why in front of the CBO and CRO. Deals that should close in Q4 slip to Q1, and you're re-forecasting constantly.
• Hiring takes forever: You need to backfill someone who left, but recruiting moves slow. You're short-handed for 2-3 months while you interview, and your team's number doesn't change.

What Success Looks Like

• Team hits 90-100%+ of quota consistently (if 5 reps at $1M each, team delivers $4.5-5M+)
• You retain top performers - low attrition on your team vs. company average
• You promote 1-2 reps per year into senior or closing roles
• Your forecast accuracy is within 10% - you commit $1M for the quarter and deliver $900K-$1.1M

Who You're Selling To

You're not selling directly - but you're coaching reps on how to engage:

• VP/Director HR, CFOs, General Counsel at mid-market and enterprise companies
• Multi-stakeholder buying committees with 3-5 people involved in decisions

Requirements

• 5-8+ years in B2B sales, with 2-3+ years as an individual contributor hitting quota
• 1-3 years as a frontline sales manager or team lead
• Experience managing 5-10 direct reports in a quota-carrying environment
• Strong coaching skills - can diagnose deal problems and give actionable feedback
• Comfortable with operational rigor (forecasting, pipeline management, CRM hygiene)
• Recruiting and hiring experience - can sell candidates and build a team