Sam Gifford

Account Executive Manager

Rillet

sales_managerBalancedConsultativeRemote📍 NYC, SF, or Remote
Deal Size: $30K-150K ACV
Sales Cycle: 2-4 months
Posted by Sam Gifford

Overview

You manage a team of 4-6 Account Executives selling Rillet's ERP to finance teams at mid-market and enterprise companies. You coach reps through deals, manage weekly forecasts, hire new AEs as the team scales, and build repeatable sales processes as GTM grows from 30 to 50+ people. This is likely a player-coach role where you carry a smaller personal quota while managing the team.


Role Snapshot

AspectDetails
Role TypePlayer-coach AE Manager (likely carrying quota)
Sales MotionManaging team doing balanced inbound/outbound
Deal ComplexityConsultative to Enterprise
Sales Cycle2-4 months (for team's deals)
Deal Size$30K-150K ACV (team average)
Quota (est.)$3-5M/year team quota + $300-500K personal

Company Context

Stage: Growth stage (140 employees, aggressive GTM scaling)

Size: 140 employees total, GTM team grew from 6 to 30 in 6 months

Growth: Hyper-growth mode - you're building management structure as the team scales. Likely adding 10-20 more GTM hires in next 6-12 months.

Market Position: Scaling a challenger brand against established ERPs - need to prove the category while building repeatable sales processes


GTM Reality

Team Structure:

  • You manage 4-6 AEs (likely growing to 6-8 as you hire)
  • Reps are mix of ramping (3-6 months tenure) and productive (6+ months)
  • Shared SC (Sales Consultant) pool supports your team on technical demos
  • Some SDR support but reps also self-source

Your Scope:

  • Quota responsibility for your team's number ($3-5M annually)
  • Hiring: Interviewing, closing candidates, onboarding/ramping new AEs
  • Deal coaching: Pipeline reviews, deal strategy, getting stalled deals unstuck
  • Process building: Documenting what works, creating playbooks, refining comp plans

Player-Coach Reality: You likely carry 15-20% of a normal AE quota ($300-500K/year) while managing. This means running 3-5 of your own deals while coaching your team on 30-40 active opportunities.


Competitive Landscape

Main Competitors: NetSuite, Sage Intacct, QuickBooks Enterprise, traditional ERPs

Management Challenge: Teaching reps how to position against entrenched incumbents, handle "we just implemented NetSuite" objections, navigate risk-averse finance buyers

Win Themes You Coach: Speed vs NetSuite, automation reducing manual close work, modern UX, better reporting for boards/investors

Loss Patterns You Fix: Deals dying in procurement, losing to "do nothing," getting stuck in endless technical evaluations, champion leaving mid-deal


What You'll Actually Do

Time Breakdown

1:1s & Coaching (35%) | Pipeline/Forecast Mgmt (25%) | Hiring & Ramping (20%) | Your Deals (15%) | Strategy & Ops (5%)

Key Activities

  • Weekly 1:1s and deal reviews: Meet with each rep to review pipeline, strategize on stuck deals, role-play demos or executive conversations. You listen to call recordings, review discovery notes, challenge their qualification. You're pattern-matching from deals you've run to accelerate their learning.
  • Forecast calls and pipeline management: Monday forecast calls with leadership where you commit your team's number. You pressure-test your reps' forecasts ("Is this really closing this quarter?"), manage slippage, identify at-risk deals. You live in the CRM ensuring pipeline hygiene and accurate stage progression.
  • Hiring and onboarding: Interview candidates (you're the hiring manager), sell them on the role, reference check, make offers. Once hired, you build their ramp plan - first 30/60/90 days, shadow calls, give them deals from the bench, coach their first few opportunities.
  • Riding shotgun on key deals: Join calls with your reps on their biggest or most stuck deals - executive presentations, pricing negotiations, procurement. You coach them real-time (Slack during calls) or debrief after to level up their skills.
  • Running your own deals: You carry a smaller book - usually the largest, most strategic opportunities or accounts that came inbound to you. This keeps you sharp and credible with the team ("I'm doing what I'm asking you to do").
  • Building repeatable processes: Document what's working - discovery frameworks, demo flows, objection handling, pricing/negotiation guidelines. Create enablement content. Work with Rev Ops on territory design, comp plan tweaks, reporting dashboards.

The Honest Reality

What's Hard

  • You're building the plane while flying it. GTM grew 5x in 6 months - there aren't established playbooks for everything. You're figuring out what works and teaching it simultaneously.
  • Managing forecast pressure from leadership while protecting your team from thrash. You commit a number Monday, then deals slip, reps miss, and you need to explain why while keeping morale up.
  • Hiring fast without dropping quality. You need to double your team in 6-12 months but can't afford bad hires who take quota capacity and create performance management headaches.
  • Some reps will struggle or wash out. You need to coach underperformers, have hard conversations, potentially manage people out if they're not improving.
  • Balancing player-coach demands - when you're deep in your own deal, your team doesn't get your attention. When you're coaching them, your personal pipeline suffers.
  • The product is evolving quickly (new features, integrations). You need to keep your team updated, handle messaging changes, manage deals that were sold on roadmap features that shifted.

What Success Looks Like

  • Your team hits 85-95% of quota (full team productivity is hard when ramping new reps)
  • Reps level up visibly - handling objections better, running tighter discovery, closing faster
  • You hire 3-4 strong AEs in the next year who ramp to productivity
  • Forecast accuracy improves over time (you call the quarter within 10-15%)
  • You build a culture where reps help each other, share wins, give honest feedback
  • Leadership trusts you to scale your team to 8-10 reps without falling apart

Who You're Managing Through

Your AEs Are Selling To:

  • CFOs, Controllers, VPs of Finance at mid-market and enterprise companies
  • Risk-averse buyers evaluating ERP replacements (high-stakes decisions)
  • Multi-stakeholder deals (finance, IT, procurement, sometimes legal/security)

Management Challenges:

  • Teaching reps to speak accounting language credibly without being accountants
  • Coaching through long sales cycles (2-4 months) where deals stall in procurement or technical evaluation
  • Helping reps handle rejection and "do nothing" losses without getting demoralized
  • Building pipeline discipline - many reps want to focus on 2-3 big deals vs maintaining 3-4x coverage

Requirements

  • 5-8+ years in B2B SaaS sales with 2-3+ years managing AEs (or strong senior IC ready to step into first management role)
  • Track record of hitting team quota and developing reps who hit their number
  • Experience selling to finance buyers or in fintech/ERP/accounting software (you need domain credibility)
  • Managed through rapid scaling (doubling team size, building processes from scratch)
  • Comfortable with ambiguity - you're building the playbook, not executing someone else's
  • Player-coach mentality - willing to carry a personal number while managing
  • Strong hiring instincts - you'll live or die by who you bring onto the team