How to Transition from Military to Sales: Career Guide for Veteran Salespeople
Military leadership to B2B sales, enterprise sales, technical sales, salary expectations, commission structure, and why veterans make great salespeople.
How to Transition from Military to Sales: Career Guide for Veteran Salespeople
Bottom Line Up Front
Military leadership = direct sales ability. You can transition to sales immediately (0-6 months to first role). Cost: $0 (no certification needed). Salary: $50K-$100K+ first year (base + commission), $100K-$200K within 3-5 years, $200K-$500K+ as top performer or sales manager. High earning potential if you're good at sales.
Your advantage: You've already been persuading people, managing teams, closing deals (military operations are deals with resources and outcomes). You understand commitment, discipline, follow-through. Those are sales fundamentals.
Why Sales Needs Veterans
Sales is about relationships, credibility, and closing deals. Veterans are naturals.
Specific advantages:
- Credibility: Military service = instant trust and respect
- Discipline: You follow process, track metrics, achieve targets
- Relationship-building: Leadership = relationship management
- Handle rejection: Military rejection is harsh; sales rejection is mild
- Under pressure: You make big decisions in chaos. Sales pressure is manageable.
- Integrity: People trust you. That's essential for long-term sales relationships
- Work ethic: You outwork civilians in competitive roles
Sales Career Paths
Path 1: B2B Sales Representative (Inside Sales)
Best for: Those wanting steady salary + commission, office-based
What you do: Call/email business clients, explain products/services, close deals. Phone/video-based.
Timeline: Immediate entry (0-3 months to hire)
Requirements:
- High school diploma
- Good communication skills
- Ability to handle rejection
- Willingness to make lots of calls
Salary:
- Base: $35K-$50K
- Commission: $15K-$50K (variable based on deals closed)
- Total year 1: $50K-$100K
- Year 3: $100K-$150K
- Year 5+: $150K-$250K (if top performer or moved to management)
Best for: Starting in sales, want predictable base salary + upside commission
Path 2: Enterprise Sales / Account Executive
Best for: Those targeting high-value clients, willing to travel, want highest income
What you do: Sell large deals to corporations. Build relationships with decision-makers. Complex, high-value sales ($10K-$500K+ per deal).
Timeline: 1-2 years in sales first, then promote to enterprise
Salary:
- Base: $80K-$120K
- Commission: $30K-$200K+ (depends on deal size, volume)
- Total: $110K-$320K+
- Top performers: $300K-$500K+
Best for: Those with leadership background, ambitious, comfortable with risk
Why veterans excel: You're already comfortable managing complex stakeholder relationships. Enterprise sales is similar.
Path 3: Technical Sales Engineer / Solutions Consultant
Best for: Those with technical background + sales aptitude
What you do: Sell technical solutions (software, systems, engineering). Explain technical details, customize solutions, close technical deals.
Timeline: Immediate for those with tech background, 6-12 months if learning tech
Salary:
- Base: $70K-$100K
- Commission: $20K-$80K
- Total: $90K-$180K
- Year 5+: $150K-$250K
Best for: Engineers/IT folks wanting sales income but leveraging technical skills
Path 4: Sales Manager / Sales Director
Best for: Those wanting to lead teams, manage other salespeople
What you do: Manage sales team, set targets, coach reps, manage performance
Timeline: 2-3 years as salesperson first, then move to manager
Salary:
- Year 1-2 (new manager): $100K-$130K (base + bonus)
- Year 3-5: $130K-$180K
- Year 5+: $180K-$300K+
Best for: Natural leaders, want to build teams, not just sell yourself
Step-by-Step Plan to Get Into Sales
Phase 1: Assess Fit (Month 1)
Evaluate:
- Are you comfortable with rejection? (Critical for sales)
- Do you like building relationships?
- Can you handle variable income? (Commission-based)
- Are you competitive / driven by metrics?
- Do you prefer inside sales (phone/email) or outside sales (travel)?
Reality check:
- Sales is high-pressure (constant quotas)
- Rejection is constant (most calls don't convert)
- Income is variable (good months, slow months)
- You need thick skin and resilience
If you're energized by competition and closure, sales is for you.
Phase 2: Research and Decide (Month 1)
Decide:
- Inside sales (B2B, phone-based) vs. Enterprise sales (travel, high-value)
- Technical sales vs. general sales
- What industry interests you (tech, finance, healthcare, manufacturing, etc.)
Research:
- Talk to 5 salespeople in your target industry
- Ask about: Income potential, lifestyle, challenges, growth
- Understand sales culture in that industry
- Identify companies you want to sell for
Phase 3: Apply (Month 2-3)
Where to find sales jobs:
- LinkedIn (search "sales representative" or "account executive")
- Indeed.com
- Company career pages (tech, finance, manufacturing, etc.)
- Recruiters (sales roles have active recruiters)
Target companies:
- Tech (Salesforce, Microsoft, Google, startups)
- Financial services
- Manufacturing (B2B)
- SaaS (Software-as-a-Service) companies
- Healthcare
- Any mid-size company with sales team
Application strategy:
- Apply to 20-30 positions
- Tailor resume to emphasize: leadership, relationship-building, goal-achievement, persuasion
- Cover letter: Explain why military leadership = sales ability
- Get references from military supervisors
Military advantage: Many companies actively recruit military for sales (discipline, credibility)
Timeline: 1-4 weeks to interviews, 2-4 weeks to offer
Phase 4: Interview (Month 3-4)
What they'll ask:
- Tell me about yourself (prepare 2-minute story)
- Why sales? (Explain your interest)
- Tell me about a time you overcame objection (use military example)
- What's your sales process? (You might not know yet—learn basic process)
- Role-play scenario (they'll give you objection, you respond)
Preparation:
- Study the company (what do they sell)
- Learn basic sales terminology (pipeline, close rate, quota, commission, etc.)
- Practice role-play (friend plays customer, you sell to them)
- Prepare questions for them (show interest)
Your advantage: Military background = automatic credibility. Just be yourself.
Phase 5: First Sales Job (Month 4+)
Entry position likely: Sales Representative, Account Executive, or Sales Development Rep (SDR)
Onboarding:
- 2-4 weeks training (company products, sales process, CRM systems)
- Mentoring by senior rep (4-8 weeks)
- Ramping up calls/activity
- First deals expected month 2-3
Your first month:
- Learning products/services
- Training on systems
- Making calls, getting rejected, learning
- Closing first deal (around month 2-3, if you're pushing hard)
Salary: $50K-$80K depending on base and early commission
Timeline to productivity: 3-4 months to start hitting quota, 6-12 months to be comfortable
Phase 6: Building Sales Career (Year 1-5)
Typical progression:
- Year 1: Sales Rep, ramping up, $50K-$80K
- Year 1-2: Hitting quota, building skills, $80K-$120K
- Year 2-3: Exceeding quota, better clients, $120K-$160K
- Year 3-4: Top performer, promoted to Senior Rep or Enterprise, $150K-$200K
- Year 4+: Sales Manager/Director or top Enterprise Rep, $200K-$400K+
How you grow:
- Hit quota consistently (shows you can sell)
- Build client relationships (long-term value)
- Take on bigger deals/accounts (higher commission)
- Develop specialized expertise
- Move into management (if interested)
Salary and Commission Structure
B2B Inside Sales Rep
| Performance | Base Salary | Commission | Total Year 1 | Year 3 | Year 5 |
|---|---|---|---|---|---|
| Below quota | $40K | $5K-$10K | $45K-$50K | $60K | $80K |
| At quota (100%) | $45K | $20K-$30K | $65K-$75K | $100K | $125K |
| Exceeds (150%) | $45K | $35K-$50K | $80K-$95K | $130K | $160K |
| Top performer (200%) | $45K | $50K-$70K | $95K-$115K | $150K | $200K |
Variables:
- Deal size (larger deals = larger commission)
- Commission percentage (3-10% of deal value typical)
- Ramp period (you might not hit quota year 1, ramping up)
- Bonus (some companies add bonus if you hit overall company quota)
Enterprise Sales / Account Executive
| Performance | Base Salary | Commission | Total Year 1 | Year 3 | Year 5 |
|---|---|---|---|---|---|
| Ramping | $80K | $10K-$20K | $90K-$100K | $140K | $180K |
| At quota (100%) | $100K | $40K-$60K | $140K-$160K | $180K | $230K |
| Exceeds (150%) | $100K | $70K-$100K | $170K-$200K | $220K | $300K |
| Top performer (200%) | $100K | $100K-$150K | $200K-$250K | $280K | $380K |
Notes:
- Enterprise deals are larger ($50K-$500K+)
- Commission % might be lower (2-5%) but deal size makes up for it
- Takes longer to ramp (3-6 months learning)
- Year 1 often below quota (learning)
Real Veteran Success Stories
Story 1: Infantry Officer to B2B Sales Rep
Major David Chen (Army, 10 years Infantry Officer)
- Background: Led troops, persuaded people, made high-stakes decisions
- Timeline: ETS age 32, decided sales appealed to him
- Path:
- Month 1-2: Applied to 25 companies
- Month 3: Got 3 offers (inside sales roles)
- Month 3: Accepted position as Sales Rep at SaaS company, $50K base + commission
- Year 1: $85K (base + commissions from 8 deals closed)
- Year 2: $115K (better at sales, closing 15 deals)
- Year 3: $165K (top performer, promoted to Senior Rep)
- Year 4: $200K+ (closing large enterprise deals, moving into account executive territory)
- Year 5: Moved to Sales Manager (managing team of 5), $140K base + $60K bonus = $200K
Why successful: Military leadership = sales skills. Persuasion skills transferred. Competitive mindset = wants to win quota. Built strong client relationships.
Key lesson: "I thought sales was smarmy. Turns out, I was already doing it in the Army—persuading people, closing operations. Sales is just more explicit about the deal."
Story 2: NCO to Enterprise Sales
SFC Maria Lopez (Army, 12 years NCO)
- Background: Managed 30 people, handled complex logistics, negotiated with contractors
- Timeline: ETS age 34
- Path:
- Month 1-2: Applied to enterprise sales roles
- Month 3: Got offers (companies love military for enterprise sales)
- Month 4: Started as Account Executive at enterprise software company, $100K base
- Year 1: $120K (ramp period, learning enterprise sales, 2 large deals)
- Year 2: $180K (hitting quota, closing $2-3M in revenue)
- Year 3: $240K (exceeding quota, managing $5M+ accounts)
- Year 4: $300K+ (top performer, company expanding territory for him)
- Year 5: Senior Account Executive / Account Director, $320K+
Why successful: Military background = trusted with large accounts. Relationship-building skills = enterprise clients love him. Risk tolerance = comfortable with variable income.
Key lesson: "Enterprise sales pays way better than inside sales, but it's harder and longer sales cycles. Worth the extra effort."
Story 3: Support Role to Sales Manager
Captain James Park (Air Force, 8 years, logistics/operations)
- Background: Operations, not direct sales, but good with people and processes
- Timeline: ETS age 30
- Path:
- Month 1-2: Applied to sales roles (realized he wanted management track)
- Month 3: Started as Sales Development Rep (SDR—qualifies leads, not closing big deals), $45K base + small commission
- Year 1: $65K (learned sales process, industry)
- Year 2: Promoted to Sales Rep (closing deals), $80K base + commissions, Total $110K
- Year 3: Promoted to Senior Rep, $100K + commission, Total $155K
- Year 4: Promoted to Sales Manager (managing 5 reps), $130K base + $40K bonus = $170K
- Year 5: Senior Manager (team of 10), $160K base + $60K bonus = $220K
Why took longer path: Started lower (SDR) to learn business thoroughly. Leadership track appealed to him. Now managing team, happier than individual contributor.
Key lesson: "I started lower because I didn't have sales background. But learning thoroughly helped me manage better. Moving to leadership was right call for me."
Common Challenges and Solutions
Challenge #1: "I'm Worried About Rejection"
Reality: Sales is rejection-heavy. Most calls don't convert.
Perspective: Military rejection is harsh (orders, life/death). Sales rejection is mild (they just say no). You can handle this.
Solution:
- Reframe rejection as data (they said no, learn why, move to next)
- Numbers game mindset (make 100 calls, 10 meetings, 2 deals = normal)
- Remember: You're not being rejected, your offer is
Challenge #2: "Variable Income Seems Risky"
Reality: Commission-based income varies month-to-month.
Solution:
- Choose inside sales with base salary first (more stable)
- Enterprise sales pays better but more risk
- Build 6-month emergency fund before starting
- Expect ramp period (first 3-6 months might be below average)
Challenge #3: "I Don't Have Sales Experience"
Reality: That's fine. Most sales reps start with no experience.
Solution:
- Company training covers basics
- You learn by doing
- Mentoring from senior rep helps
- First 6 months is learning curve
Challenge #4: "I Don't Like the Aggressive Sales Culture"
Reality: Sales culture can be aggressive/competitive.
Solution:
- Some companies are less aggressive (healthcare, education, nonprofits)
- Inside sales is less aggressive than enterprise/field sales
- You can set your own tone with clients (build relationships, not just push sales)
- Find company culture that matches your style
Action Plan
Month 1: Decide
- Decide: inside vs. enterprise sales
- Choose industry of interest
- Research 5-10 companies you want to work for
Month 2-3: Apply
- Apply to 25-30 sales roles
- Prepare resume emphasizing leadership, relationships, goal-achievement
- Interview with companies
- Negotiate offer
Month 3-4: Accept Role
- Start first sales job
- Complete onboarding/training
- Shadow experienced rep
Months 5+: Ramp Up
- Start making calls/pitches
- Close first deals
- Hit quota targets
- Build client base
FAQ
Q: How quickly can I make good money in sales? A: Year 1: $50K-$100K. Year 2-3: $100K-$150K. Year 4+: $150K-$300K+ if you're good.
Q: Is sales for everyone? A: No. You need comfort with rejection, competitive drive, and ability to handle variable income. But if you're comfortable with these, sales pays very well.
Q: Do I need any certifications? A: No certifications required. Sales is learned through doing.
Q: What's the difference between inside and enterprise sales? A: Inside sales: phone/email, office-based, $50K-$150K. Enterprise: travel, face-to-face, large deals, $150K-$500K+.
Q: Can I transition to management from sales? A: Yes, very common. Top performers often become sales managers.
Next Steps
- This week: Talk to 3 salespeople about their careers
- This month: Apply to 25-30 sales roles
- Month 2: Interview, get offers
- Month 3: Start first sales job
- Month 4: Begin making calls, closing deals
Resources:
- Sales job boards: LinkedIn, Indeed, SalesHiring.com
- Companies: Salesforce, Microsoft, Google Cloud, Slack, Twilio, HubSpot, any mid-size company
- Learning: Sales blogs, podcasts ("The Sales Hacker," "Hubspot Sales Podcast"), YouTube
- CRM tools: Salesforce, HubSpot, Pipedrive (most companies use these)