VP of Sales — GreenLeaf SaaS

## Mission Help mid market sales teams close more without adding headcount. ## Vision A world where every revenue team runs on signal, not vibes. ## Core Values - Customer obsession - Frictionless onboarding - Honest data, even when it stings - Speed beats perfect - Win as one team

Mission GreenLeaf replaces spreadsheets for mid market accounting teams with a workflow they actually want to use. Why this hire matters now We are at the natural ceiling of a pure SMB motion. Without a mid market hire we plateau at $22M. The current AE team burns out trying to push deals upmarket they were not hired to sell. What success looks like in 12 months $32M ARR. Mid market motion repeatable. Lean team. CFO does not have to ask the CEO what next quarter looks like. Stakeholders aligned on this - CEO (Maya): Sponsor. The candidate's most active partner. - CFO (Jordan): Wants forecasting discipline most. Will sit in on Round 1. - Head of SDR (Ravi): The candidate's first internal report. Will sit on Round 3. - Board: Reviewed and approved this search Apr 12.

Two profiles fail here. The enterprise only seller who treats SMB AEs like junior versions of themselves. The SMB only operator who underestimates a 6 month mid market cycle. We have hired both. Both left within 14 months.

VP of Sales, GreenLeaf SaaS Reports to: CEO Location: Remote (US, ET preferred) About GreenLeaf We help mid market accounting teams replace spreadsheets with a workflow they actually want to use. $18M ARR. 6 AEs. Profitable. Well capitalised. The SMB motion works. Mid market is next. The role You own new logo revenue. $18M to $32M in 12 months. You inherit a working SMB engine and a good head of SDR. You build the mid market motion from the ground up. The playbook. The first two reps. The early deals. You will love it here if you are: - Comfortable in a forecast call with our CFO - The kind of leader who reads call notes, not just dashboards - Direct. Low ego. Built multi segment teams before What you will not be doing: - Building a 50 person sales org. We stay lean. - Selling into Fortune 500. That is not our wedge. Compensation Base $230k to $260k. OTE $440k to $500k. Equity. Real benefits. If interested Send a short note about a mid market motion you built from scratch. References from former direct reports get to the front of the line.

30 days. Listen. - 1:1 with every AE, SDR, and CS lead - Sit on 20 customer calls (live or recorded) - Audit the SMB playbook end to end with the head of SDR - Read the last 12 lost deal post mortems - One memo to the CEO: "What I am seeing" 60 days. Diagnose. - First draft of the mid market motion: ICP, qualifying questions, pricing - Pipeline review cadence locked in (weekly with team, biweekly with CEO) - First mid market AE search opened, or first internal candidate confirmed - One deliberate experiment running 90 days. Build. - Mid market AE hired and ramping - Forecast discipline live. Two clean weekly forecasts in the books - Q3 plan approved by board - First mid market deal in late stage pipeline 6 months. Compound. - Mid market motion books at least $1.5M in pipeline - First closed-won mid market logo. Document the pattern. - AE productivity up 20% versus baseline (deals per quarter per rep) - Net retention holds 118% or better across the SMB book 1 year. Set the next bar. - $14M new ARR booked. Pipeline coverage at 3.2x for next quarter. - 9 rep team retained intact plus mid market lead onboarded and ramped - The forecast methodology is the source of truth used by the board - Write the FY playbook the next hire inherits

Where this person exists Not at the big name unicorns. Look at: - Series B and C SaaS that recently expanded into a new segment (Gong, Klaviyo, Ramp 3 years ago) - Former AEs at Toast or ServiceTitan who became leaders elsewhere - Mid market sales leaders at Intercom, Front, Pendo who are stuck under a peer cap Title patterns to search - "VP of Sales" + "mid market" + Series B keyword in LinkedIn - "Head of Mid Market" at companies $15M to $60M ARR - "Director of Sales" at companies past Series C who got passed for VP Companies to target (12 anchors) Front, Pendo, Hubspot (mid market division), Drift, Outreach, Salesloft, Mixpanel, Heap, Iterable, Klaviyo, Customer.io, Help Scout. Companies to avoid Anyone who came up only at Salesforce or Oracle. They will not adapt to a 6 person team.

Touch 1. LinkedIn connect, no pitch. Short note: "Saw your mid market work at [Company]. Building something adjacent at GreenLeaf. Would value 15 min when timing is right." Touch 2. Personal email, no pitch (day 3). "Curious if you have ever built a mid market motion in a company that started SMB. We are doing it now. No ask. Just a swap of notes." Touch 3. InMail with a real reason (day 7). Reference something specific from their company's recent earnings or job postings. Touch 4 to 6. Spaced 5 to 7 days apart. Share a Loom of our product. Share the actual mid market POV. Show them what they are walking into. Touch 7 to 9. Mike's voice memo intro. If they are warm, Mike records a 2 minute Loom. Stops being scripted. Touch 10. "Closing the loop" email. "Last note from me. We are taking three finalists to round two next week. If timing is wrong, all good, and good luck with your build." Touch 11. Quarterly re engage. Bookmark for 90 days out. Most great hires happen on touch 14, not touch 4.

Round 1. Mike + the hiring manager (45 min). Goal: Is the bar there? Walk away with a clear yes or no on "could this person lead the team." Questions: 1. Tell me about the last mid market motion you built. Walk me through month 1, month 6, month 12. 2. The last time you had to fire a rep who was missing number but well liked. What was the lead up? 3. What does your weekly cadence look like with your top AE versus your bottom AE? 4. What is the smallest number on your forecast you have ever defended to a board, and what happened? Round 2. Working session (90 min). Goal: Watch them think. Bring them inside the actual problem. Pre work: Send them our last 4 lost mid market deals (sanitised). Ask for a 1 page POV on what we got wrong. In the session: 1. Walk us through the POV. 2. We role play one of those deals. They are the AE. The CFO is asking "why now." 3. We share our actual Q2 forecast and ask: "What would you change about how this is built?" Round 3. The team (60 min, no Mike). Goal: Do the people who will work for them say yes? Two AEs plus the head of SDR. Open agenda. Their feedback is binding.

Two from former direct reports. Non negotiable. Questions for direct reports: 1. What did they actually do for your career? Specific moment, not a platitude. 2. When they coached you on a deal you were losing, what did they say? 3. Where did they fall short as a manager? Walk me through one example. 4. Would you work for them again? Why or why not? One from a former peer (another VP). Questions: 1. In forecast calls, were they the optimist or the realist? 2. Did they protect their team or push their team? 3. Did they leave the org better than they found it? One from a former CEO or board member. Questions: 1. Did you hire them again at another company, or recommend them? Why or why not? 2. What was the single biggest miss? Red flags to listen for - Vague answers, especially on "what did they coach you on" - Anyone who talks more about results than about people - Long gaps in the work history that do not match the resume

Offer Base: $250,000 Variable: $250,000 at 100% of plan, paid quarterly Equity: 0.45% over 4 years, 1 year cliff Sign on: $40,000 (one time, clawback if voluntary exit under 12 months) Benefits: Full medical, dental, vision. 401(k) match up to 4%. Unlimited PTO (we actually take it). Start date: First Monday of June, 2026 Counter offer prevention We have already addressed: - Comp ceiling. Equity outside the offer band if board approves Year 2 expansion - Title. VP is real, not honorary. Reports to CEO. - Team. First mid market AE search starts week one. You own it. When the current employer counters, we will know in 48 hours.

The counter offer is coming. Plan for it now. Step 1. Before the offer goes out, ask the candidate: "When you tell your current company, what is the most they will offer to keep you?" Get the number. Step 2. Beat that number on something they cannot match. Not just salary. Equity, scope, title, autonomy. Step 3. Compress the decision window. "We want an answer by Friday end of day so we can close out the search." Long windows kill more offers than low comp. Step 4. When the counter offer happens, and it will, call the candidate immediately. "I expected this. Here is what they cannot give you that we can." Pre arm them with the language to say no. Step 5. Day 1 commitment. Board introduction, first big customer call, real ownership of week one. The thing that pulls them in.

Day 1 KPI handover By end of day 1, the new VP of Sales has: - Direct access to every sales dashboard, every customer call recording, the CFO model - A 1:1 booked with every AE, SDR, CS lead in week 1 - The "last 12 lost deals" memo from the head of SDR, read together - Time blocked on the CEO's calendar for end of week debrief - The mid market AE job spec, ready to post if they approve it

30 / 60 / 90 review cadence Day 30. CEO plus new VP. One question: "What is the biggest thing you have seen that we are not yet talking about?" Memo back to the team. Day 60. Same, plus: "What needs to change in how we are running the SMB engine, even though it is working?" Make it safe to challenge. Day 90. Three way with the board chair. "Are we on track for the $32M number? What do we need to decide now?" Day 180. Optional pivot point. If the answer is no to the $32M number, the board hears it from the VP, not from Mike. That is the bar.

Week 1 to 2. Build the search. Kit complete. Role posted on 3 channels. Outreach started. Week 3 to 6. First 15 candidates screened. Mike plus hiring manager screen weekly. Top 6 advance. Week 7 to 8. Round 2 working sessions. 3 candidates take the pre work. 2 advance to team round. Week 9. Team round plus references. Final 2 meet the team. Reference checks run in parallel. Week 10. Offer. Counter offer ready before the offer goes out. Week 11 to 12. Close and start.