Sales teams that win. Careers that last.
Sales teams that win. Careers that last.
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Built for a complex, high-stakes sales environment that needs independent operators, a unified GTM language, and leadership capacity returned to where it belongs.
CityBlock doesn't have a revenue problem. You already count 5 of the 6 largest insurance companies in the country as customers. Typical deal values run $100M to $200M annually, and you closed 9 deals last year. What you have is a capacity and leverage problem. You now own all of GTM, sales, account management, and implementation, and the only way that works long-term is if sales can run without you having to drive every deal. Right now, it can't.
Your existing team can execute the process. What they can't yet do is own the strategy, drive it externally, and influence up and down the chain without you in the room. Add three incoming reps from an acquisition whose selling style doesn't match the CityBlock standard, and you have a team that's going to absorb your time rather than free it, unless something changes structurally.
Your team knows the process. But knowing the process isn't the same as independently driving the deal, shaping the narrative externally, influencing stakeholders above the buyer, and making strategic calls without escalating to you. That gap is where your time goes.
The internal influence piece isn't a soft skill, it's a capacity issue for you. Every time a rep can't navigate an internal alignment conversation on their own, it lands on your desk. That's the specific skill gap that's costing you the most bandwidth.
Three incoming reps from an organization that closed 1-2 deals across their entire tenure. Your team closed 9 last year. That's not a ramp problem, it's a methodology gap. Without a structured integration, these reps default to the way they already sell instead of the CityBlock way.
Sales, AM, and implementation are three separate worlds right now. You want them speaking the same language, not just collaborating better, but operating from a shared framework for how CityBlock wins and retains business. That alignment doesn't happen on its own.
You said it directly: a rubric that tells people what to do until it becomes second nature. Right now, standard of excellence lives in your head and in what you model. That knowledge has to be codified, transferable, and self-reinforcing when you're not in the room.
Leads are largely inbound or generated by you and your boss. You have a Director 60 days in whose entire job is top-of-funnel development, but she hasn't yet gotten into independent outreach and pitching. That's the first output you need from the team, and she needs structure to get there.
| Rep | Readiness | Situation | CoMission Approach |
|---|---|---|---|
| Director A Top of Funnel |
Building | 60 days in. Needs to get moving on outreach and pitching. The ramp is expected, she's not behind, she just hasn't started. Mike's explicit 30-day goal: three new customer pitches. | Structure and accountability for the first 30 days. Identify what's blocking outreach, build the cadence, and get reps on the board. Three pitches in 30 days is the measurable outcome we hold her to. |
| Director B ~1.5 Years In |
Strong | Knows the process cold. Strong internal relationships. The gap is financial fluency and the ability to independently drive strategy externally and influence senior leaders, inside and outside CityBlock, without Mike as backstop. | Develop the strategic layer on top of a solid process foundation. Financial storytelling, executive influence, leading conversations where the stakes are high. The goal is she runs deals Mike never has to touch. |
| Senior Manager | High Upside | Punching well above his weight. Knows everything in and out. Already leading smaller deals start to finish. The gap is confidence, he has the knowledge, he just needs the reps and the belief that his voice belongs in the room. | Reps and reinforcement. Build the confidence that matches the competence that's already there. He's the future, the investment here compounds fast. |
| Acquisition Rep 1 | Incoming | Arrives approximately August. Background suggests a higher-volume, more transactional environment, less consultative than CityBlock's. Coachability is the open question until we assess. | Diagnostic in the first 30 days. Assess against the CityBlock standard: strategic thinking, financial fluency, stakeholder influence. Fit call within 60 days if the profile doesn't support development. |
| Acquisition Rep 2 | Incoming | Same context as above. Three reps from the same environment; patterns will likely be consistent. We're optimistic based on the feedback Mike's received, but the assessment has to drive the plan. | Same diagnostic approach. Integrate what's coachable, document what isn't. Mike shouldn't be carrying the judgment calls on these hires, CoMission takes ownership of the assessment and the recommendation. |
| Acquisition Rep 3 | Incoming | Same context. Three is a cohort, which creates both an integration opportunity and a risk, they can reinforce each other's habits, good or bad. That dynamic needs to be actively managed. | Manage the cohort dynamic deliberately. Avoid the huddle. Integrate them individually into the CityBlock team, not as a bloc that maintains the old way of selling. |
Most programs make reps better. We make the system that develops and evaluates reps better. The capability and accountability layer is where CityBlock's gap lives, and that's precisely where we operate.
We don't arrive with a pre-built program. We've already built working hypotheses from what you told us. Coaching and rubrics are built around your specific breakpoints, not a generic curriculum.
Multi-stakeholder, long-cycle, outcome-driven sales is our native environment. We understand the discipline required to influence a $100M+ decision and how to build that discipline in a team.
You said it: a rubric that tells people what to do until it becomes second nature. That's the deliverable we're wired for. Not a training event. A transferable standard the team can carry on its own over time.
Sales, AM, and implementation speaking the same language isn't a one-day workshop. We build the shared framework deliberately, with the same rigor we bring to the selling side.
On the acquired reps, you need a clear read within 60 days, not a guess. If a rep isn't the right fit for the CityBlock standard, we say so directly, with documentation, and a recommended path.
You floated a 90-day sales-only trial before expanding to AM and implementation. That's the right shape. It's the easiest yes, it de-risks the decision internally, and it lets us prove the model before the scope grows.
CoMission embeds with the existing sales team and leads the integration of the three incoming acquisition reps. The 90-day objective is the structure built and running: independent deal ownership taking hold, a shared methodology in place, the operating rhythm live, and clear fit decisions on the new hires before those calls get harder to make. We stay in the seat running it with you from there, not hand you the keys and walk.
Once sales is finding its footing, CoMission expands into the alignment work you want across all three GTM functions. The shared language, the cross-team rubric, and the collaborative operating model that turns Mike from the linchpin of every handoff into the strategic leader above it. Most engagements run six to twelve months, and the goal we hold ourselves to is the teams owning the standard by the nine to twelve month mark, then a deliberate step-down. How long is your call.
Your team gathers in Columbus on 7/21 and 7/22. If it's useful, we'd love to be there ahead of the formal late-August start to meet the account management and implementation teams in person. Totally your call, but in our experience meeting face to face early is what makes everything after it land. We'd join as part of the engagement, not as an extra.
All timelines measured from engagement start date.
Full diagnostic of the current team. Individual rep assessment, deal ownership, financial fluency, external influence capability, pipeline contribution. Working hypotheses on the three acquisition reps as soon as they arrive. Development plans drafted for all three existing reps.
Director A into independent outreach and pitching cadence. Three new customer pitches tracked and debriefed. Operating rhythm established, weekly cadence with Mike, individual rep 1:1s running. CityBlock methodology onboarding begins for acquisition reps the moment they land.
Coaching cadence fully running for all six. Director B working on financial storytelling and executive influence. Senior Manager taking on additional deal ownership with CoMission support. Acquisition reps assessed against the CityBlock standard, where they are and what it'll take.
Written fit assessments on all three acquired reps delivered to Mike, clear recommendation, documented. First draft of the CityBlock sales rubric complete. Mike gets back measurable capacity: fewer escalations, fewer deal check-ins, fewer judgment calls landing on him by default.
You floated 10 to 30k, and since that was an honest guess with no fractional engagement to compare against, value is the real anchor here, not the number. So here's the plain shape of it. Phase 1 is a fixed 90-day build: we install the structure, integrate the acquired reps, and get sales running. From there we stay in the seat running it with you while the team grows into the new pattern, and when you're ready, the engagement broadens to all of GTM. Two numbers, no open meter: $18K to build and lead sales, $25K to run the whole thing.
Focused coaching and accountability for your existing three. Structured cadence, individual development plans, and a first version of the rubric. Straight with you, though: this tier is light on the acquisition integration and fit work, so with three reps landing in August, it leaves the part that matters most right now uncovered.
The complete Phase 1 build. Existing team development, acquisition integration and assessment, the full rubric, and the operating cadence that takes the day-to-day off your plate while we run sales with you. This is the foundation everything else builds on.
The broadening you described. We keep running sales with you while the team grows into the new pattern, and bring account management and implementation into the same language and the same rubric. One operating model across the customer lifecycle, you leading it, us steering until the new way holds. You decide how long that takes, not a meter.
Why not just hire a CRO? Because you were just handed GTM. A CRO sits over or beside that mandate, costs $350K to $500K loaded with equity, takes six months to hire and ramp, and is permanent. CoMission is temporary by design. We build the structure, run it with you, and step back when the team holds the standard on its own. You stay the leader. We're the tool that gets you there, not a chair on the org chart. Phase 1 is a fixed $54K over 90 days, and even full GTM at $25K a month lands well under a loaded executive hire, with a planned exit instead of a salary line that renews forever.
This isn't a seat on your org chart. It's training wheels. The entire point is to install the capability, the rubric, and the operating rhythm, then hand the bike back and let your team ride. We measure success by how quickly you stop needing us in the room.
That's why this has a target, not an open meter. Phase 1 is a fixed 90 days. From there, most engagements run six to twelve months, and the goal we hold ourselves to is simple: have it running, and you running it, by then. Some clients keep us longer, and if you do, we shift to a lighter advisory cadence. How long is always your call. When the standard holds without us driving it, we step back on purpose. You're hiring an outcome you set the timeline on, not a seat that quietly auto-renews.
| Option | Cost | Time to Impact | What You're Actually Getting |
|---|---|---|---|
| Hire a CRO | $350K to $500K loaded, plus equity | 6 months to hire and ramp | A permanent executive over the GTM mandate you were just handed. Equity, severance risk, and political overlap with your own role. You're betting two quarters on one hire made under pressure while the acquired reps land untrained. |
| Sales Training Program | Varies | One event | Fades in two weeks. No accountability layer. No system change. Doesn't touch the acquisition reps. Doesn't build the rubric. Doesn't free Mike's time. |
| Do Nothing | $0 now | n/a | Three acquisition reps arrive in August with no integration plan. Existing team stays dependent on Mike. The GTM alignment work never gets done. Mike stays the linchpin for all three functions. |
| CoMission | $54K for the 90-day Phase 1 then $25K / month to run all of GTM, when ready |
Operational in week one | Embedded development for all six reps. Acquisition integration and fit calls. The rubric built and running. Your escalation load drops, and we stay in the seat with you until the team owns the standard. No ramp, no overhead, no flight risk, and a planned exit. |
