Overview
You're the first sales manager hire under a CRO who's 3 days into the job. You'll manage a small team of BDRs and AEs selling cybersecurity and compliance services while carrying 50-60% of a full sales quota yourself. This is a build-from-scratch role: creating process, coaching reps, and proving what works. If you want a fully-baked sales org with established playbooks, this isn't it.
Role Snapshot
| Aspect | Details |
|---|---|
| Role Type | Player-coach hybrid (managing + selling) |
| Sales Motion | Balanced - building outbound engine while managing inbound/self-sourced |
| Deal Complexity | Consultative to Enterprise |
| Sales Cycle | 2-4 months (AE deals you'll close personally) |
| Deal Size | $25K-150K+ per deal |
| Quota (est.) | $500-700K personal + team quota responsibility |
Company Context
Stage: Bootstrapped/Private (20+ years in business, 135 employees)
Size: 135 employees
Growth: Brand new CRO (3 days in) building first real GTM infrastructure - this is a transformation moment
Market Position: Established firm (900+ clients) but not top-tier brand - historically delivery-focused, now investing in revenue growth
GTM Reality
Pipeline Sources:
- Outbound (building from scratch with new BDRs)
- Self-sourced by AEs (current state, needs structure)
- Inbound leads (small volume, needs routing and qualification process)
SDR/AE Structure: You're defining it. Currently hiring BDRs and AEs - you'll decide how leads route, what qualifies as a handoff, how territories work.
SE Support: No dedicated SEs - AEs pull in technical delivery team as needed. You may need to define when/how that happens.
Competitive Landscape
Main Competitors: Coalfire, Schellman, A-LIGN, Prescient Assurance, regional compliance firms, Big 4 for enterprise
How They Differentiate: 20 years of experience, 900+ clients, integrated security + compliance approach
Common Objections: Price, incumbent vendors, timeline concerns, scope uncertainty
Win Themes: Track record, comprehensive approach, industry expertise
What You'll Actually Do
Time Breakdown
Managing Team (30%) | Closing Your Own Deals (30%) | Building Process (25%) | CRO/Leadership Alignment (15%)
Key Activities
- Coaching and managing reps: Daily check-ins with BDRs on activity and messaging. Weekly pipeline reviews with AEs. Listening to calls, reviewing emails, giving feedback. Helping reps unstick deals. This is hands-on coaching, not just reporting on dashboards.
- Closing your own deals: You'll carry a smaller book of opportunities (likely larger/strategic accounts) and run them through close. This keeps you credible with the team and helps you understand what's working in the market.
- Building sales process and playbooks: What's the discovery framework? What does a good proposal look like? How do we price and scope deals? What objection handling works? You're documenting this as you go, not inheriting it.
- Hiring and onboarding: You'll likely hire 2-3 more reps in first 6 months. Writing JDs, screening candidates, running interviews, onboarding new hires. Probably no formal onboarding program yet - you're building it.
- Forecasting and reporting: Weekly forecast calls with CRO. You're accountable for team pipeline health, conversion rates, and hitting team number. Early on, your forecast will be directional at best until you have data.
- Aligning with CRO on strategy: New CRO is forming opinions on ICP, pricing, comp plans, territory structure. You're a sounding board and executor. Expect frequent strategy pivots as you both learn what works.
The Honest Reality
What's Hard
- Player-coach time split is brutal: Managing a team well is a full-time job. Closing deals is a full-time job. You're doing both. Something will suffer - usually your own deals or your personal life. You'll work 50-60 hour weeks.
- Building process while running the business: You don't have time to step back and design perfect systems. You're building the plane while flying it. Processes will be messy and evolve constantly.
- Managing up to a brand new CRO: He's 3 days in and figuring out the business. Priorities will shift. Strategies will change. You need to be adaptable and okay with ambiguity.
- Reps will struggle (and quit): You're hiring into a brand-new team with no proven playbook. Some reps won't hit quota. Some will leave. You'll feel responsible for their success and failure.
- Limited resources: No sales ops, no enablement team, no marketing support (probably minimal). You're doing CRM admin, building your own reports, creating your own training materials.
- Defining "good" is hard: What's a good connect rate for BDRs in this market? What's a realistic deal close rate? You're figuring out benchmarks as you go.
What Success Looks Like
- Hit your personal quota ($500-700K) while building a team that closes $1.5-2M+ collectively in year one
- Hire and ramp 3-5 reps who stick around and start performing by month 6
- Build repeatable process (talk tracks, email templates, proposal templates, qualification framework) that new reps can follow
- Establish forecast accuracy within 20% by quarter 3-4
- Prove what works so the company can scale the team further
Who You're Selling To
(Same buying committee as AE role)
Primary Buyers:
- CISOs / VP of Security
- Compliance Managers/Officers
- CFOs / COOs (approval)
- IT Directors (mid-market)
What They Care About:
- Audit success on first attempt
- Minimal internal disruption
- Transparent pricing and scope
- Vendor credibility and experience
- Timeline certainty
Requirements
- 5-7 years in B2B sales, with at least 2-3 years managing a team (preferably in services, consulting, or complex solutions)
- Proven track record carrying quota AND coaching reps to hit theirs
- Experience building sales process from early stage (you've done this before at a startup or in a turnaround)
- Comfortable with ambiguity and rapid change - this is not a structured corporate environment
- Strong closing skills - you'll be managing deals personally and modeling for the team
- Cybersecurity or compliance industry experience helpful but not required (you'll learn quickly)
- Player-coach mentality - willing to roll up sleeves and do rep-level work when needed
- Ability to operate without sales ops, enablement, or heavy marketing support