Enterprise Sales Manager Hiring Guide
ZYTHR Resources •
September 19, 2025
TL;DR
Defines role expectations, sourcing and screening strategies, interview questions, rejection reasons, evaluation rubric, selling points, red flags, and a 90-day onboarding plan tailored to enterprise sellers.
Role Overview
The Enterprise Sales Manager is responsible for acquiring and expanding strategic, high-value accounts (typically mid-market to Fortune 100). They manage the full sales cycle—from prospecting and qualification through negotiation and close—often coordinating cross-functional teams (pre-sales, legal, customer success) to deliver bespoke solutions. Typical expectations include owning a multi-million dollar quota (ARR or ACV), driving predictable pipeline, and developing long-term executive relationships.
What That Looks Like In Practice
Day-to-day this person builds targeted account plans, runs executive-level demos, manages RFP processes, and negotiates complex contracts. Success metrics include quota attainment, average deal size, sales cycle length, win rate against competitors, and net revenue retention for accounts they influence. They spend time on strategic outreach, opportunity qualification calls, internal alignment meetings, and executive sponsorship activities to close deals involving multiple stakeholders.
Core Skills
These are the non-negotiable technical and domain capabilities to include in the job description and screen for during interviews.
- Enterprise selling experience Proven track record closing multi-stakeholder, multi-quarter deals with ACV or ARR relevant to your business. Preferably 5+ years in enterprise accounts or hunter roles.
- Quota attainment Consistent performance against quota for multiple quarters/years. Ask for specific attainment percentages and deal sizes.
- Account planning & territory management Ability to build and execute account plans, prioritize named accounts, and manage a territory to generate predictable pipeline.
- Negotiation & contract experience Comfort with commercial terms, SOWs, pricing models, discounts, and procurement/legal processes common to large buyers.
- CRM & stack fluency Proficient in Salesforce or preferred CRM, and sales engagement tools (Outreach, Salesloft), with strong pipeline hygiene and forecasting discipline.
- Solution & product knowledge Ability to position complex solutions to technical and business audiences; translate value into ROI and business outcomes.
Rate candidates on each skill with concrete examples (past deals, metrics, tools used).
Soft Skills
Enterprise roles require high-caliber interpersonal skills—evaluate these through behavioral interviews and role plays.
- Executive presence Comfort engaging C-level executives and articulating strategy, ROI, and risk in concise terms.
- Stakeholder management Ability to map stakeholders, influence without authority, and keep complex buying committees aligned.
- Resilience & persistence Enterprise cycles are long; the candidate should demonstrate discipline in follow-up and managing long timelines.
- Collaboration Works effectively with pre-sales, product, legal, and customer success to remove blockers and accelerate closes.
- Problem-solving Creative approaches to tailoring proposals for unique buyer requirements and overcoming procurement obstacles.
Look for examples where these skills materially influenced deal outcomes.
Job Description Do's and Don'ts
A clear, accurate JD attracts the right senior sellers. Do's emphasize outcomes and candidate fit; don'ts avoid vague or off-putting language.
| Do | Don't |
|---|---|
| Specify quota, target ACV/ARR, and typical deal size | Use vague phrases like 'help grow sales' without metrics or scope |
| List required enterprise sales experience and industry or product context if essential | Include unnecessary junior requirements (e.g., '2 years sales experience') that contradict seniority |
| Be transparent about compensation range and structure (base + OTE) | Hide comp or provide misleading 'competitive' without ranges |
| Call out cross-functional responsibilities and decision-making autonomy | Overload the JD with unrelated responsibilities (product management, marketing ops) |
Use the do's when crafting your posting and the don'ts as pitfalls to remove.
Sourcing Strategy
Target candidates who have sold to similar buyer profiles, industries, and deal sizes. Prioritize quality over volume.
- LinkedIn Recruiter boolean searches Search for titles like 'Enterprise Account Executive', 'Strategic Account Executive', 'Senior Sales Manager' combined with product/industry keywords and competitor company names. Filter for recent quota attainment signals.
- Target competitor / adjacent vendors Source sellers from companies that sell complementary or competing solutions—those reps understand buyer processes and established relationships.
- Referrals & internal networks Ask sales leaders and top performers for referrals — frontline referrals often yield culturally aligned, high-performing candidates.
- Executive-focused job boards & events Use industry conferences, executive networking events, and paid placements on sales leadership boards to find senior sellers.
- Recruiting firms specialized in enterprise sales Engage a specialist search firm for hard-to-fill or senior quota-carrying roles where ramp speed and fit are critical.
- Alumni networks & customer-facing talent Consider customer success, solutions engineering, or renewals leaders who have sold upmarket or have strategic account relationships.
Track conversion rates from each channel to optimize outreach spend.
Screening Process
Design a screening funnel that confirms enterprise capability, quota performance, cultural fit, and role-specific know-how before progressing to senior interviews.
- Recruiter screen (30 minutes) Confirm basic qualifications: target verticals, quota size, deal sizes, reason for leaving, authorization to work, and compensation expectations. Validate energy and excitement for the role.
- Hiring manager phone screen (30–45 minutes) Behavioral questions about recent enterprise deals, pipeline generation tactics, and specific evidence of quota attainment. Discuss territory and ICP alignment.
- Sales skills exercise / case study (home or live, 60 minutes) Ask for an account plan or a tailored pitch/demo to a hypothetical enterprise buyer, including objection handling and a negotiation approach.
- Panel interview with cross-functional stakeholders (45–60 minutes) Include pre-sales, customer success, and a product leader to assess collaboration, technical positioning, and ability to drive complex deals.
- Reference checks & compensation discussion Speak to at least two references (manager and peer/customer) verifying performance claims and style. Finalize offer and negotiate contract terms.
Keep each stage time-boxed and communicate next steps clearly to candidates.
Top Interview Questions
Q: Describe the largest enterprise deal you closed. What was your role and how did you influence the outcome?
A: Look for specific metrics (ACV/ARR, deal length), the candidate's direct actions (stakeholder mapping, executive engagement), obstacles encountered (procurement, legal), and how they overcame them. Good answers show ownership, strategy, and measurable impact.
Q: How do you build pipeline in a new territory with no existing relationships?
A: Strong responses include targeted account research, multi-channel outreach (executive intro, referrals, events), tailored value propositions, and quick pilot or proof-of-value strategies to accelerate engagement.
Q: Tell me about a time you lost a strategic deal. What happened and what did you learn?
A: Assess for candid reflection, lessons learned, and process changes implemented afterwards (e.g., earlier procurement involvement, better stakeholder mapping). Avoid candidates who deflect blame.
Q: How do you work with pre-sales and product when requirements don’t map cleanly to your offering?
A: Ideal candidates describe collaborating to scope a tailored solution, managing expectations with the customer, and using pilots or phased rollouts to de-risk the buyer.
Q: Give an example of negotiating complex commercial terms. How did you protect margin while closing the deal?
A: Seek negotiation tactics: trade-offs offered (term, scope, success metrics), approvals process used, and how they preserved pricing integrity while securing close.
Top Rejection Reasons
Deciding rejection reasons ahead of time makes screening objective. These are the common deal-breakers to screen for during early interviews.
- No enterprise sales evidence Candidate lacks history of closing multi-stakeholder, high-value deals or the stated quotas are for smaller, transactional sales not aligned with the role.
- Inconsistent quota attainment Patchy or unexplained performance history across multiple quarters or lack of verifiable metrics to back claims.
- Poor stakeholder/influence examples Can't demonstrate how they influenced executive buyers, aligned committees, or managed complex buying groups.
- Weak collaboration with cross-functional teams Reluctance or inability to work with presales, product, legal, or customer success—critical in enterprise deals.
- Cultural or ethical concerns Behavior that suggests poor fit with company values, aggressive or deceptive tactics, or inability to handle sensitive negotiations professionally.
Document reasons in your ATS to keep hiring decisions consistent and defensible.
Evaluation Rubric / Interview Scorecard Overview
Use a consistent rubric to compare candidates objectively. Score each criterion 1–5 and capture notes and examples for calibration.
| Criteria | Score (1-5) | Evidence / Notes |
|---|---|---|
| Track record of enterprise quota attainment and deal sizes | 1-5 | Documented quota %, typical ACV/ARR, example deals |
| Sales process & pipeline management | 1-5 | CRM usage, forecasting accuracy, examples of account planning |
| Executive engagement & stakeholder influence | 1-5 | Examples of C-level interactions, steering committees, sponsors secured |
| Collaboration & cross-functional execution | 1-5 | Work with pre-sales, legal, CS; stakeholders' feedback when available |
Require panel members to submit scores before calibration to avoid groupthink.
Closing & Selling The Role
Senior sales candidates evaluate opportunities carefully. Use these points to sell the role effectively and win top talent.
- Clear comp and upside Be transparent about base, OTE, accelerators, and realistic ramp timeline. Show OTE mechanics with example attainment scenarios.
- Autonomy & strategic ownership Emphasize ability to own a territory/account list, influence GTM motions, and shape enterprise strategy.
- Product-market fit & customer success stories Share strong case studies and references showing measurable ROI and recent enterprise wins.
- Career path & leadership opportunities Discuss potential to grow into a senior AE, left- or right-seat leadership, or regional sales leadership roles.
- Support & enabling infrastructure Highlight pre-sales support, marketing demand generation, legal enablement, and tools that reduce administrative burden.
Tailor the pitch to the candidate's motivations—comp, career growth, autonomy, product market fit.
Red Flags
Watch for behaviors or gaps that typically predict friction or poor performance in enterprise roles.
- Vague deal descriptions Unable to quantify role in wins or provide verifiable details about past deals and stakeholders.
- Blame-heavy stories Consistently blames others for losses without acknowledging lessons or personal responsibility.
- Overpromising on product capabilities Tendency to promise unvetted features or bypass product/legal, which risks delivery and reputation.
- Unwillingness to use formal sales processes Resists CRM discipline, forecasting cadence, or cross-functional reviews required for enterprise scale.
- Frequent short tenures Multiple short roles without credible explanations can indicate churn risk or inability to close long-cycle deals.
Onboarding Recommendations
A structured onboarding accelerates ramp and early wins. Aim for a 90-day plan tied to measurable outcomes.
- Day 1–30: Foundation and product immersion Complete product training, competitive landscape, buyer persona sessions, CRM setup, and meet key internal partners (pre-sales, CS, legal). Assign initial shadowing with top AEs.
- Day 31–60: Prospecting and pilot pipeline Execute a targeted outreach plan to identified strategic accounts, run discovery calls, and create 2–3 account plans. Begin engaging pre-sales for demos and proof-of-concept scoping.
- Day 61–90: Close focus and quota readiness Drive at least one pilot or POC, progress one or more opportunities to negotiation, finalize territory/account plan, and review a performance plan with quota milestones and coaching touchpoints.
- Ongoing: Continuous enablement Monthly coaching, deal reviews, access to recorded best-practices sessions, and a development plan for skills like executive selling and contract negotiation.
Assign a ramp mentor and schedule regular 1:1s to track progress against milestones.
Hire an Enterprise Sales Manager who consistently closes large deals
Use this guide to define the role, source targeted candidates, run objective screens, and evaluate finalists so you hire someone who can hit quota, shorten sales cycles, and scale relationships with strategic accounts.