VP Sales - SaaS
Kaiko Systems
About the Role
We are looking for a hands-on VP of Sales to lead our commercial operations through an important growth phase. You will own revenue delivery, pipeline accuracy, and team performance as we continue to scale and accelerate that growth by building on the foundations we have.
This role requires someone who can quickly assess our current commercial operations, implement structured qualification frameworks, and drive systematic improvements across the sales organization. You'll need to operate as strategist, architect, and executor, bringing discipline and structure to accelerate our revenue trajectory.
This role is for someone who has successfully scaled sales teams in early-stage or growth-phase SaaS companies, implementing repeatable processes and accountability where rapid execution is essential.
What You'll Do
Immediate Priorities (First 90 Days)
- Assess and optimize pipeline health: Conduct comprehensive review of all active opportunities to ensure accurate forecasting and prioritize high-probability conversions.
- Implement qualification discipline: Install MEDDPICC (or equivalent) across all deals and establish weekly pipeline review cadence to ensure evidence-based forecasting.
- Enhance conversion strategies: Develop and execute specific strategies to improve trial-to-paid conversion rates. Work key opportunities directly while coaching the team.
- Refine go-to-market approach: Analyze win/loss patterns to sharpen ICP definition and improve targeting accuracy across marketing and sales.
- Evaluate team capabilities: Assess current team performance, identify development needs, and determine optimal team structure for our growth targets.
Building the Foundation (Months 4-6)
- Align marketing and sales: Establish clear lead qualification criteria and handoff processes to maximize team efficiency and focus on high-potential opportunities.
- Document repeatable processes: Create structured customer journey frameworks and sales playbooks for qualification, objection handling, and deal acceleration.
- Optimize sales operations: Implement or enhance CRM systems and forecasting tools to improve pipeline visibility and reporting accuracy.
- Build enablement infrastructure: Develop onboarding materials, call frameworks, and competitive positioning to accelerate new hire productivity.
Scaling for Growth (Months 7-12)
Deliver on revenue targets
- Establish product feedback mechanisms: Create structured process to communicate validated market insights to product team, ensuring roadmap alignment with customer needs.
- Scale team strategically: Expand sales capacity thoughtfully as revenue model proves repeatable, prioritizing quality over speed.
- Create sustainable systems: Document processes, develop team leads, and establish accountability structures that enable consistent performance.
What You'll Need to Bring
- 5+ years B2B SaaS sales experience with at least 2 years in a player-coach or sales leadership role (team lead, sales manager, or small VP role). You've run deals yourself AND managed others doing the same.
- Complex, multi-stakeholder deal experience: You've closed deals with €20K-€100K ACV where you had to navigate procurement, technical stakeholders, and C-suite sign-off. Deal cycles of 2-6 months. You can show concrete examples of how you implemented qualification frameworks (MEDDPICC, MEDDICC, or similar) and improved forecast accuracy from sub-60% to 80%+.
- Forensic mindset: You've conducted win/loss analyses, audited pipelines, or diagnosed why teams were missing targets. You dig into CRM data, challenge assumptions, and deliver hard truths to leadership, even when it's uncomfortable.
- Hands-on execution: You've personally closed at least €500K-€1M+ in ARR while simultaneously coaching or managing a team. You're not a "strategy only" leader, you'll work deals yourself if that's what it takes.
- Startup or scale-up experience: You've worked in at least one company under 100 people where you had to build processes from scratch, operate without perfect data, and move fast with limited resources. You know the difference between "building" and "optimizing."
Highly valuable:
- 3-5 years in maritime, logistics, industrial tech, or similarly technical B2B sectors: You understand buyers who need ROI proof, have long evaluation cycles, and require deep product knowledge. Bonus if you've sold into shipping companies, port operators, or supply chain organizations.
- Turnaround track record: You've significantly improved sales performance and turned team members into consistent performers within 6-12 months. You can explain what you changed and why it worked.
- Technical founder collaboration: You've worked closely with product-led or engineering-led founders. You know how to translate customer feedback into actionable product insights without overwhelming the roadmap, and you can balance "we need this feature to close deals" with "we need to sell what we have."
- Lean operator mentality: You've built sales systems with Google Sheets or basic CRMs before upgrading to expensive tools. You've run effective sales meetings without consultants, built onboarding programs without L&D teams, and created forecasting models without RevOps. You know how to get 80% of the result with 20% of the budget.
If you're reading this and thinking "I've done most of this, but I'm missing X or Y"—still apply. We'd rather talk to someone with 80% of the profile who's hungry and resourceful than someone with 100% who needs perfect conditions to operate.
What You Will Get
- Direct impact: Your work will determine whether this company hits its targets or misses badly
- Autonomy: Diagnose the problems, propose the solutions, execute the plan
- Supportive leadership: CEO understands the problems and is ready to act on hard truths
- Upside: Equity participation that reflects the turnaround nature of this role