B2B: Sales Hiring & Leadership Cheat Sheet

20+ FREE GTM & RevOps Cheat Sheets Get the latest cheats sheets & guides in your inbox ✉️
Org Design & Structure
Sales Team Evolution 🪴 CRO Organization 🤹🏻 Org Design Best Practice
ARR Stage Sales Team Structure Key Focus Key Challenges 1. Define roles and responsibilities clearly — avoid overlap (esp. between AE/AM/CS)
CRO CFO 2. Align comp plans with the motion — hunters vs. farmers need different incentives
$0–$1M Founder-led sales Validate product-market fit Low brand trust 3. Territory design matters — rotate/freeze accounts carefully to avoid rep churn
No formal sales team (may add a CS) Close first paying customers No repeatable process 4. Keep span of control tight — 6–8 direct reports max per frontline manager
Ad hoc process Understand ICP Limited data or customer proof
5. Invest in RevOps early — messy data = messy decisions
6. Integrate CS/AM into GTM — revenue doesn’t stop at closed-won
$1–$5M 1–3 AEs Build repeatable sales motion Inconsistent messaging Customer Revenue
Founder still involved Narrow ICP and value prop Founder bottlenecks Marketing Sales FP&A 7. Plan for evolution — what works at $10M won’t scale to $50M
Success Operations
May add first SDR or CS Start building a pipeline High CAC and long cycles

$5–$15M Dedicated AEs by segment (SMB/MM) Scale what works Hiring at pace
SDR function emerging
First Sales Leader
Specialize roles (AE/SDR/CSM)
Standardize onboarding & enablement
Forecasting still unreliable
Skill gaps in sales team
Org Design Archetypes
Marketing Ops Sales Ops CS Ops
Model Best For Cautions
$15–$30M Mid-size sales team (10–30) Improve win rates Plateauing productivity
Sales Ops + Enablement Formalize pipeline management Systems complexity increases
Manager layer forms Build cross-functional GTM playbook Onboarding time extends Segmented (SMB/MM/ENT) Companies with diverse Requires clear rules of engagement and comp
ACVs and sales cycles alignment

$30–$60M Sales pods by vertical/region Drive operational excellence Process compliance Geo-Based (East/West) Global go-to-market or Needs strong playbook consistency and enablement
Layered leadership (Directors) Expand into new verticals Territory conflict regional buyers across regions
Full RevOps team Mature forecasting & QBRs Balancing scale vs customization

Pod-Based (SDR+AE+SE) Velocity-oriented orgs Pod output may vary; requires strong management
$60–$100M Global/regional GTM orgs Land strategic logos Org silos (esp. MM) and alignment
Strategy & Pricing & Deal
Deep specialization (SEs, overlay roles, Expand ACV via multi-threading Culture dilution Enablement Data & Analytics Business Systems
channel, etc.) Tight alignment with Product & CS Maintaining agility while scaling structure Planning Desk Product-Line Based Multi-product companies Can create siloed behavior — needs RevOps and CS
with unique buyers to unify motion

Hiring

Sourcing AE Hiring Profile by Segment Sales Manager Profile (First-Line)

Referrals Outbound Sourcing Recruiters Segment Ideal AE Profile Sales Skill Success Traits Red Flags Interview Questions Scorecard Criteria Category Details
Requirements
Why it works: Why it works: Why it works:
Top reps know other top reps. Referral- A-players are rarely on job boards. Strategic Well-connected recruiters and niche Ideal Profile 3–7 years of sales experience
based hiring yields faster closes, higher outbound targeting allows you to handpick communities offer filtered access to high-
SMB 1–3 years Fast qualification/ Hustler mentality Needs a lot of hand- “Tell me about a time you Activity level 1–3 years of people management
retention, and better cultural alignment. based on past performance, stage fit, and caliber talent and often know who’s
domain experience. quietly looking. experience disqualification Thrives in holding had to hit quota with little Time to first deal Has carried a quota
How to do it well: High-volume, Efficient pipeline autonomy Doesn’t thrive in high enablement.” Average deal cycle Experience in coaching full-cycle reps
Incentivize employee referrals (cash, How to do it well: How to do it well: transactional management Strong activity activity environments “How do you manage 50+ Win rate in high Ideally promoted internally or managed 5–10 reps in SaaS
bonuses, spiffs) Build shortlists of reps crushing quota at Work with 1–2 specialized sales recruiters SaaS or SDR Product pitching discipline Overcomplicates opps in pipeline?”
Ask top performers, “Who’s the best relevant companies (use tools like (not generalists) who know SaaS inside promotion track simple deals Primary Mission Drive team quota attainment
seller you’ve worked with?” Bravado, Sales Navigator, Clay) and out Develop talent and improve rep productivity
Use hiring managers’ networks — have Target those with experience in similar Tap into peer-led communities like SaaS
Improve forecasting accuracy and deal inspection
them share JD on LinkedIn with ACV, deal cycles, and market Sales Talent, Thursday Night Sales, SDR
personal context Craft personalized outreach: “We’re Nation, or Bravado Mid-Market 3–5 years Discovery & Analytical but fast Weak qualification “Walk me through how you Pipeline coverage
Create a warm outreach template for scaling a team to hit $100M ARR — your Attend or sponsor micro-events (dinners, experience objection handling paced discipline qualified a deal that looked accuracy Success Traits Player/Coach mindset
execs to share in peer groups (e.g., background at [Company] caught my Zoom panels, AMAs) to meet reps Full-cycle sales Deal progression & Self-starter with Lacks urgency promising but fell through.” Discovery & High EQ and coaching discipline
Pavilion, RevGenius) eye.” passively open to new roles ownership forecasting coaching openness Overwhelmed by “How do you coach a qualification Process and CRM hygiene obsessed
Experience in 30– Champion building Strong pipeline complexity or champion?” Forecast accuracy Can manage up and down effectively
Bonus Tip: Use tools like Teamable or Cord Bonus Tip: Use Gem or TopFunnel for Bonus Tip: Treat recruiters as extensions of 90 day cycles hygiene ambiguity
to mine LinkedIn connections and automate automated, multi-touch outbound cadences your brand — arm them with your mission,
Key 1:1 rep coaching (calls, skills, mindset)
warm intros. that mimic top-of-funnel sales. sales culture deck, comp plan, and growth
story. Responsibilities Pipeline inspection and forecast management
Hire, onboard, and ramp reps
Enterprise 5–10+ years Executive Long-cycle Leans too much on “Tell me about your last 6– Strategic account
Enforce sales process and deal progression
experience presence endurance brand name logos 12 month sales cycle. Who execution
Partner with Enablement, RevOps, and Marketing
Multi-threaded Deal orchestration Cross-functional Can’t clearly explain were the stakeholders, and Deal size &
Stats selling Strategic account fluency deal mechanics how did you drive complexity
Red Flags Over-indexes on numbers, under-indexes on people
Navigated planning Political navigation Avoids accountability urgency?” Ability to multithread
complex orgs and skills for losses & manage long-cycle Can’t explain how they improve rep performance

6-10
referral candidates are of hires via
3-4x 30-50%
advanced Too tactical, no strategic thinking
long cycles opportunities
more likely to become Outbound interview stage/ AE "Hero seller" syndrome (still wants to close deals themselves)
top performer Sourcing (LinkedIn) hire

Best Practices Common Hiring Mistakes AE Onboarding Framework Manager Onboarding Framework
Area Best Practices Mistake Why It Happens Consequences Resolution Phase Focus Areas Key Activities Milestones / Success Phase Focus Areas Key Activities Milestones / Success
Criteria Criteria
Define the Role Write stage-appropriate job descriptions (not aspirational Hiring Too Urgency to fill headcount Wrong hires cost time, Use a consistent scorecard &
Clearly fluff) Fast (Gut over leads to skipping steps morale, and revenue run all candidates through the
Clarify ownership, scope, stage, and success metrics Process) or misalignment full loop, even under pressure Days 1–30 Foundational Company mission, values, Certified on product & ICP Days 1–30 Understand the Learn team Can articulate team
upfront Knowledge & GTM strategy Passed discovery & demo System & Observe strengths/weaknesses performance gaps
Hiring for Overvaluing brand logos Misalignment with your Assess behavioral traits + stage Alignment Product deep dive & role-play the Team Understand GTM motion, CRM, pipeline & forecast
Scorecard- Use structured interviews tied to a scorecard competitive landscape Logged 10+ call shadows and
Resume, Not or big-company stage → overbuilt process, fit (e.g., $100M rep in a $10M playbooks, CRM dashboards proficiency
Driven Hiring Assess consistently across all candidates Sales process & CRM self-review
Fit experience without poor adaptation org needs adaptability) Shadow pipeline & forecast Completed 1:1s with every
Evaluate traits, not just experience training
contextual fit reviews rep & cross-functional
Shadow top reps Meet with cross-functional peers partner
Sell the Articulate your GTM vision, growth story, and culture
Vague or Overly generic, not tied Attracts mismatched Define what success looks like in
Mission Great sellers want to sell for someone they believe in
Fluffy Job to outcomes applicants or disqualifies the 3, 6, 12 months — make it
Days 31– Applied Learning & Start outbound prospecting Owns 20–30% of quota Days 31–60 Start Coaching & Run 1:1s and pipeline reviews Coaching plans in place for
Descriptions right ones measurable
Structured Run a tight loop: Recruiter > Hiring Manager > Panel > Exec 60 Light Execution or owning inbound opps Logged 5+ qualified opps Driving Process Implement daily/weekly cadences all reps
Process Add role-specific challenges (mock calls, deal breakdowns, Run discovery and co-pilot Pipeline hygiene and CRM Discipline Reinforce sales process stages Leads team forecast with
etc.) Skipping Sales Relying only on Poor read on actual ability Add mock demo, deal review, or demos compliance score of 80%+ Align with Enablement on rep accuracy
Simulations interviews and talk to sell, coach, or lead coaching session depending on Weekly coaching with development Operational cadences (1:1s,
role manager forecast, standups) in motion
Team Let reps or managers participate in peer interviews
Involvement Helps assess team fit and buy-in Pipeline building rituals
Not Testing Mistaking confidence for Difficult to develop or ramp Ask for feedback loops, “What’s
for competence quickly the best feedback you’ve Days 61–90 Drive Lead team toward quota targets Team performance trending
Reference Always do backchannel checks (ideally with shared
Coachability received — and how did you Days 61– Full Ownership & Running full-cycle opps At or near quota pacing Performance & Partner with RevOps/ Product/ upward
Checks connections)
apply it?” 90 Quota Execution Regular 1:1s for deal Runs deals solo end-to-end Influence Strategy Marketing Improvements in win rate or
Ask “Would you rehire this person again?”
inspection Completes win/loss analysis Identify top/bottom performers sales velocity
Account planning on closed deals Contribute to org-level strategy Drives hiring plans or territory
Bias Run a pre-brief to align interviewers on what “great” looks Ignoring Red Rushing or trusting Rehires or problem Always do 2–3 backchannel
Time management & discussions optimization
Calibration like Flags in candidate narrative too performers sneak through checks — former peers, bosses,
territory prioritization recommendations
Avoid hiring “mirror image” personalities Backchannels much or customers if possible

Sales Leaderhip & Culture Benchmarks

Sales Culture & Values Compensation Benchmarks (US) Hiring Benchmarks

Core Value How It Shows Up in Sales Early Warning Signals Segment Base Salary OTE Quota Category Metric / Benchmark Typical Range / Value Source
Range
Accountability Reps own their pipeline, forecast, and follow-up Reps blame Marketing, Product, or CS for lack of results
Missed targets lead to learning, not excuses Forecasts consistently off Ramp & Tenure Average AE ramp time 4.5 – 6 months The Bridge Group, 2023 Sales Development
Managers coach to performance, not just activity “Happy ears” culture around deals Report
SMB AE $55K–$75K $100K–$130K $400K–$600K
Curiosity Reps ask thoughtful discovery questions beyond surface pain Discovery calls feel like interrogations or jump to demos
Average AE tenure ~18 months RepVue, Sales Hacker, Gartner
Deep understanding of buyer personas and ICP Reps can’t articulate the customer’s “why now”
Deal notes show clear problem/opportunity mapping Pipeline filled with unqualified or low-fit deals
Mid-Market AE $70K–$90K $150K–$180K $700K–$1M % of reps leaving before hitting full productivity 26% The Bridge Group
Velocity Clear next steps after every meeting Deals stall with no clear reason
Reps proactively unblock bottlenecks No urgency in follow-up or next steps
Quota & % of AEs hitting quota ~53% Salesforce State of Sales, Forrester, CSO
Time spent on high-probability, high-fit deals Long sales cycles with poor conversion
Enterprise AE $90K–$140K $200K–$300K+ $1.2M–$2M+
Performance Insights

Collaboration Frequent syncs with CS, Product, and Marketing Tension between sales and other teams
Shared goals across GTM teams Missed handoffs or inconsistent messaging % of team revenue driven by top 20% 50–60% Xactly, Forrester
Reps advocate for customer needs internally Internal finger-pointing after churn or missed deals
Sales Manager $100K–$130K $180K–$240K+ Team quota:
$2M–$5M+ Typical quota attainment spread (low → high 30–150% of quota RepVue, Pavilion Data
Learning Obsessed Weekly learning rituals like call reviews or win/loss analysis Same mistakes repeated across the team performers)
Peer coaching and shared best practices Enablement is seen as a checkbox, not a resource
Reps seek feedback from managers and teammates No sharing of new tactics or insights in team settings
(Source: RepVue, OpenComp, Betts Recruiting) Hiring Funnel Avg. time to hire a quota-carrying AE 45–60 days LinkedIn Hiring Benchmarks, Betts Recruiting

Termination Best Practices

Avg. candidates interviewed per AE hire 5–8 LinkedIn Talent Solutions, Bravado Insights
VP of Sales Benchmarks
Step Action Details / Best Practices Offer acceptance rate 40–60% Greenhouse, Lever Benchmark Reports
Stage Base Salary OTE Equity Range
1. Identification Recognize consistent underperformance, misconduct, or misalignment Use objective data: quota attainment, pipeline metrics, feedback trends Sourcing & % of high performers sourced via referral or >60% TopFunnel, Gem, Bravado
$1M–$5M ARR $160K – $180K $250K – $300K 0.5% – 1.0% Channels outbound
2. Documentation Keep detailed records of performance, feedback & behavioral issues Use 1:1 notes, CRM activity logs, coaching recaps, performance reviews
% of AEs found through job boards <15% Betts Recruiting, Gartner
3. Formal Warning Deliver a PIP (Performance Improvement Plan) or final written warning Set clear 30/60/90 day goals; align on outcomes required to retain role $5M–$20M ARR $180K – $200K $300K – $400K 0.3% – 0.7%

% of best reps actively looking ~20% Pavilion, LinkedIn Talent Solutions

4. HR/Legal Review Loop in HR/People Ops before formal action is taken Ensure compliance with labor laws, term contract clauses & severance policy

5. Termination Conduct a live (or video) meeting with manager + HR Be concise, respectful, and clear — don't argue or rationalize Cost & Impact of Estimated cost of a bad sales hire 3–5x OTE Sales Assembly, Xactly, OpenView Partners
$20M–$50M $200K – $225K $350K – $450K 0.15% – 0.4%
Meeting ARR
Mis-Hire

6. Exit Logistics Revoke access, collect equipment, handle commissions/severance Follow checklists for email, CRM, Slack, devices, pipeline reassignment Impact on pipeline from an underperforming AE $500K–$2M in stalled/lost pipeline Internal RevOps benchmarks from OpenView,
Bessemerdata
7. Internal Share transparent, professional notice to team Frame it as a performance/culture misalignment to reduce speculation $50M–$100M $225K – $250K+ $400K – $500K+ 0.05% – 0.2%
Announcement ARR
Post-Hire % of companies with formal AE onboarding ~40–50% The Bridge Group, SaaStr Surveys
Onboarding programs
8. Debrief / Learning Internal retro: was it hiring, onboarding, enablement, or coaching gap? Feed insights back into recruiting, onboarding, and team coaching playbooks

Revenue Intelligence powered by AI

Activity Capture Conversation Intelligence Pipeline Management Sales Forecasting