VP of Sales Hiring Guide
ZYTHR Resources •
September 19, 2025
TL;DR
This guide covers role expectations, core and soft skills, sourcing and screening strategies, interview questions, rejection criteria, evaluation rubrics, closing tips, red flags, and a recommended onboarding plan for a VP of Sales.
Role Overview
The VP of Sales is the senior leader responsible for creating and executing the go-to-market sales strategy, building and coaching a high-performance sales organization, owning quota attainment, and aligning sales activities with company growth goals. This role partners with marketing, customer success, product, and finance to drive predictable revenue, optimize processes and compensation, and expand into new markets or segments.
What That Looks Like In Practice
Leading a team of account executives, SDRs, and sales managers to hit quarterly targets; implementing scalable sales processes and CRM governance; designing territory plans and compensation programs; hiring and developing leaders; negotiating large deals and key partnerships; reporting pipeline health and forecast to the executive team and board.
Core Skills
A great VP of Sales combines strategic planning with hands-on execution. Prioritize skills that drive revenue, scale teams, and create repeatable processes.
- Revenue strategy and forecasting Builds multi-quarter revenue plans, establishes reliable forecasting discipline, and translates company goals into attainable sales objectives.
- Sales leadership and team building Hires, mentors, and scales A-player sales reps and managers; builds clear career paths and performance expectations.
- Go-to-market design Defines segments, ICP, sales motions (inbound, outbound, channel), territory design, and compensation to maximize coverage and ROI.
- Pipeline and CRM management Implements CRM best practices, consistent stage definitions, pipeline hygiene, and metrics to ensure forecast accuracy and lead conversion.
- Dealcraft and negotiation Leads complex, enterprise negotiations, structures creative deal economics, and protects margin while accelerating close velocity.
- Cross-functional collaboration Partners with marketing for demand generation, product for roadmap prioritization, and customer success for retention and expansion.
- Data-driven decision making Uses sales analytics to measure performance, optimize funnel conversion, and steer investment in people and tools.
Candidates rarely excel in every area; weigh skills against your company stage and go-to-market model.
Soft Skills
Soft skills determine if a candidate can lead change, inspire teams, and operate with the rest of the leadership team.
- Executive presence Comfortable presenting to the CEO, board, and investors; communicates vision and tradeoffs succinctly under pressure.
- Coaching mindset Develops people through clear feedback, structured 1:1s, and hands-on training; prioritizes talent development.
- Resilience and adaptability Navigates ambiguity, pivots GTM approaches when required, and maintains team morale through change.
- Influence without authority Builds alignment across functions, negotiates resource tradeoffs, and secures buy-in for sales initiatives.
- Customer empathy Understands customer problems deeply, uses insights to shape messaging, positioning, and product feedback.
Assess these through behavioral interviews and references rather than just a resume.
Job Description Do's and Don'ts
Your job description should attract the right senior leaders and set clear expectations. Avoid vague or conflicting language.
| Do | Don't |
|---|---|
| State clear responsibilities (revenue targets, team size, P&L ownership, key cross-functional partnerships). | Use vague phrases like 'help grow sales' without metrics or scope. |
| Specify required experience relevant to your stage (e.g., scaling ARR from $5M to $50M, building enterprise sales). | List an exhaustive laundry list of every possible skill; it deters good candidates. |
| Call out the most important deliverables for the first 90–180 days (hire roles, establish forecast, implement CRM cadence). | Mix strategic and tactical responsibilities without clarifying seniority; avoid asking for 'doer' and 'leader' tasks equally. |
| Be explicit about compensation structure components (base, OTE range, equity band, commission plan philosophy). | Hide compensation or give unrealistic ranges; it wastes time for both sides. |
Use the Do column when writing your JD and avoid items in the Don't column.
Sourcing Strategy
Targeted sourcing ensures you find VPs with the right stage experience and network.
- Executive search and retained recruiters Use for senior hires when confidentiality, speed, and access to passive candidates matter. Provide clear scorecards and company context.
- LinkedIn network mapping Map current VPs/Heads of Sales at competitors and adjacent markets; use mutual connections for warm introductions.
- Customer and partner referrals Ask key customers, channel partners, and board members for introductions — they often know proven leaders in your space.
- Scaling company alumni pools Source leaders from companies that recently scaled similarly to your target stage (e.g., SaaS scaling from $10M to $100M).
- Industry events and executive communities Network at relevant conferences, invite prospects to advisory sessions, and participate in industry roundtables.
Prioritize channels that surface leaders with relevant domain, buyer-channel, and scale experience.
Screening Process
A disciplined, staged interview process reduces risk and surfaces behavioral evidence of past performance.
- Initial recruiter screen (30 minutes) Confirm interest, compensation expectations, notice period, top accomplishments, stage/segment fit, and logistical eligibility. Gate for deal sizes, team sizes led, and repetition of success.
- Hiring manager / CEO conversation (45–60 minutes) Assess strategic thinking, go-to-market vision, cultural alignment, and high-level plan for first 90–180 days. Evaluate interpersonal chemistry with CEO.
- Case study / take-home assignment Provide a realistic GTM problem (territory design, ramp plan, compensation structure, or pipeline acceleration). Review for logic, metrics, and execution detail. Prefer a time-boxed deliverable to avoid overburdening candidates.
- Functional deep-dive with sales leaders (60 minutes) Assess sales process design, CRM governance, hiring philosophy, coaching approach, and deal desk/ops collaboration.
- Cross-functional interviews (product, marketing, customer success) Validate collaboration style, ability to influence priorities, and commitment to retention/expansion.
- Reference checks (targeted) Speak with former managers, direct reports, and at least one peer. Ask about quota history, hiring outcomes, culture fit, and how they handle missed targets.
- Final compensation and culture alignment with CEO/board Close on expectations for OTE, equity, plan accelerators, and mutual success criteria before offering.
Keep rounds focused, limit interviewer overlap, and move quickly to maintain candidate momentum.
Top Interview Questions
Q: Describe a time you scaled a sales organization. What were the most important decisions you made and what were the measurable results?
A: Look for specifics: starting ARR and ending ARR, team size before/after, hiring plan, churn/NRR impact, processes added, and concrete outcomes tied to those decisions.
Q: How do you build a sales forecast and what steps do you take when a forecast is slipping?
A: Ideal answers show a repeatable forecasting model, leading indicators monitored (pipeline coverage by stage, conversion rates), and a playbook for recovery: deal reviews, resource reallocation, or promotional tactics.
Q: Tell me about a time you fired or replaced a senior sales rep or manager. How did you handle it and what was the outcome?
A: Expect evidence of objective performance management, clear documentation, coaching attempts, communication skills, and what metrics improved post-change.
Q: What is your approach to designing compensation plans? Give examples of trade-offs you made between base, commission, and accelerators.
A: Good candidates discuss simplicity, pay-for-performance, alignment to company goals (new logo vs expansion), quota setting, and examples of behavior changes driven by plan re-design.
Q: How do you partner with marketing to improve lead quality and conversion?
A: Seek tactical examples showing SLAs, ICP alignment, joint campaigns, lead scoring, and closed-loop reporting that improved conversion and CAC efficiency.
Q: What would your 90-day plan look like if you accepted this role?
A: Strong answers include listening tours, data and process audits, quick wins (forecast accuracy, top-opportunity focus), hiring priorities, and clear KPIs for 90/180 days.
Top Rejection Reasons
Decide rejection criteria ahead of interviews to avoid bias and make faster, consistent choices. Below are common, defensible reasons to pass.
- No repeatable revenue track record Candidate cannot point to sustainable, repeatable outcomes (not one-off success) or lacks metrics demonstrating consistent quota attainment at comparable scale.
- Mismatch in stage experience Has only experience at enterprise incumbents but no evidence of building processes in high-growth or early-stage environments (or vice versa) depending on your needs.
- Weak people leadership Cannot describe clear hiring, retention, or development outcomes; references indicate high attrition or poor manager capability.
- Poor cultural fit or misaligned incentives Values or working style conflict with company culture, or their compensation expectations are misaligned with the company's ability to pay and equity philosophy.
- Inability to collaborate cross-functionally Has history of operating in silos, causing product or marketing friction that harmed go-to-market outcomes.
Use these as evaluation gates and document examples during interviews to justify decisions.
Evaluation Rubric / Interview Scorecard Overview
Use a standard scorecard to compare candidates objectively across key dimensions. Score each area and capture evidence.
| Criteria | What to look for | Score (1-5) |
|---|---|---|
| Revenue Outcomes | Demonstrated ARR growth, quota attainment history, churn/NRR impact with concrete numbers. | 1–5 |
| Team Building & Leadership | Hiring track record, retention metrics, leadership development, and ability to scale managers. | 1–5 |
| Go-to-Market Strategy | Clarity of segmentation, motion selection, territory design, and past success implementing GTM changes. | 1–5 |
| Execution & Process | CRM hygiene, forecast accuracy improvements, pipeline management, and playbooks created. | 1–5 |
| Cultural & Cross-Functional Fit | Evidence of collaboration, communication style, and alignment with company values. | 1–5 |
Aggregate scores and qualitative notes determine fit; require at least one strong reference on revenue outcomes.
Closing & Selling The Role
Senior candidates evaluate the opportunity as much as you evaluate them. Sell the mission, the runway, and the path to impact.
- Paint the vision and measurable impact Describe the company trajectory, market opportunity, and the specific revenue targets and levers the VP will own and influence.
- Be transparent on comp and equity Share base, OTE ranges, equity bands, commission structure, and accelerators. Discuss upside and realistic timing for liquidity if relevant.
- Outline autonomy and decision rights Clarify hiring authority, budget control, and which strategic decisions require CEO/board approval.
- Highlight support and resources Explain existing team capabilities, sales ops/marketing support, hiring budget, and product roadmap alignment to reduce ramp risk.
- Discuss success milestones Agree on 30/60/90 and 6/12 month goals tied to compensation or equity vesting triggers where appropriate.
Address compensation transparently and outline success metrics for the role.
Red Flags
Watch for behaviors or signals that predict poor long-term fit or execution risk.
- Vague, anecdotal answers Cannot produce specific metrics, names, or documented programs for past achievements; relies on high-level platitudes.
- Short-tenure pattern without context Multiple brief stints at companies with no clear explanation or evidence of positive outcomes in the time held.
- Blaming others for failure Avoids ownership and cannot show lessons learned from missed targets or failed initiatives.
- Overemphasis on process over people Focuses exclusively on tools and dashboards without evidence of coaching, hiring, and culture-building.
- Unrealistic promises Promises outsized revenue increases without a clear plan, resources, or understanding of the current funnel dynamics.
Onboarding Recommendations
A structured onboarding plan accelerates time-to-value. Provide clear expectations, access to data, and early wins.
- Week 1: Listening tour and data access Introduce the VP to direct reports, sales ops, marketing, product, and top customers. Provide immediate access to CRM, pipeline reports, forecast history, and compensation plans.
- Days 15–30: Audit and quick wins Deliver a succinct audit of sales process, top deals, and forecast health. Identify 1–3 quick wins (pipeline cleansing, top-opportunity plays, compensation tweak) and execute them.
- 60–90 days: Hire and structure plan Finalize hiring priorities for the next 6 months, propose territory and quota changes, and implement initial coaching cadences and scorecards.
- 90–180 days: Operationalize GTM Roll out updated compensation/territory plans as needed, formalize the forecasting cadence, and present a 12-month revenue plan to the executive team and board.
- Ongoing: Metrics and leadership development Set recurring 1:1s, leadership offsites, and a development plan for direct reports. Monitor KPIs (quota attainment, pipeline coverage, ARR growth, churn/NRR) monthly.
Review progress against milestones frequently and adjust support as needed.
Hire a High-Performing VP of Sales
Use this guide to define the role, screen candidates efficiently, and onboard your next VP of Sales so they ramp quickly and deliver predictable revenue growth.