Dagster Labs — GTM Engineer Take-Home

GTM Engineering Plan: FinServe Group

How I'd arm the AE to close a $58K expansion — from research and CRM setup through outreach, signals, and a scalable workflow for every account after this one.

PART 1

Account Selection

Why FinServe Group

PART 2A

Research & Enrichment

What data do we need?

We need to identify key people and their teams to build a complete account map:

Where we source it — internal first

Because FinServe is already a customer, we have a significant advantage: a lot of this data likely already exists in our systems. Third-party sourcing is the fallback, not the starting point.

Step 1
Internal Data (CRM + Call Recordings)
Step 2
Usage Data (Common Room)
Step 3
Fill Gaps (Clay Enrichment)
Output
Account Map / Org Chart

Step 1 — Internal Data (Salesforce + Call Recordings): Start by searching our existing CRM data and call recordings. The compliance officer's "need better lineage" comment came from a meeting — that means there's likely a recording, notes, or a CRM activity log with their name. Same for the risk team's onboarding request. Check Salesforce contact records on the account, meeting notes, CS/AM call logs, and any existing account plans. This is the fastest and highest-confidence path to identifying these people.

Step 2 — Usage Data (Common Room): Pull product usage data from Common Room for the FinServe account. Which users are most active? What features are they using? Are there any users from outside Maria Santos' immediate team already logging in — especially anyone from risk management or compliance? This usage data gets aligned with the people data from Step 1 so the account map shows not just who the decision-makers are, but how they (or their teams) are already engaging with the product.

Step 3 — Fill Gaps (Clay): For any contacts we can't identify from internal sources, run a People Search in Clay. Filter by FinServe Group + titles containing "Risk," "Compliance," "Trading," "Data Engineering," "VP Technology." Use Clay's waterfall enrichment (Apollo → ZoomInfo) to pull verified email, phone number, LinkedIn profile URL, and current job title. This is the fallback for any gaps — not the primary source.

Salesforce (CRM data) Call Recordings Common Room (usage) Clay (enrichment) Apollo ZoomInfo

The Deliverable: Account Map

The output of this research is an Account Map / Org Chart of all identified decision-makers and end-users. Each contact record includes:

Key principle: As an existing customer, FinServe's data is already largely in our ecosystem. We leverage internal sources first (CRM, call recordings, product usage) and only go to third-party enrichment tools to fill gaps. This is faster, more accurate, and reflects how a GTM Engineer should work an expansion account differently than net-new.

PART 2B

CRM Setup

Account & Opportunity Structure

The FinServe Group account already exists in Salesforce from the original deal. We don't need to create it — we need to add the expansion opportunity alongside the existing one.

Object
Details
Notes
Account
FinServe Group (existing)
Already in Salesforce from original deal
Opportunity #1
Original Dagster+ deal — $78K ARR
Existing. Contract expires end of Q2
Opportunity #2 (new)
FinServe Group — Expansion (Risk Team + Enterprise Features) — $58K ARR
Stage: Qualification · Close: End of Q1

Custom Fields

The expansion opportunity should carry the key intelligence from our account research as custom fields, pulling from the data points we already have:

Field
Value
Source
Champion
Maria Santos (Lead Data Engineer)
Existing CRM data
Economic Buyer
VP of Technology
Existing CRM data
Current ARR
$78K
Salesforce
Expansion Opportunity
Risk team (+30 seats) + Enterprise features (lineage, compliance reporting) = ~$58K ARR
Account research
Budget Cycle
Q1 budget closes end of quarter — decision imminent
Meeting notes / CS intel
Contract Expiry
End of Q2
Salesforce
Health Score
Green
Common Room / CS

Account Map

The core artifact — a visual buying committee map showing the org structure, each contact's deal role, their known need, and current engagement status. This gets linked or embedded in the Salesforce account record.

VP of Technology
Economic Buyer · Budget authority
Not Yet Engaged
Maria Santos
Lead Data Engineer · Champion
Engaged — Current power user
Compliance Officer
TBD via call recordings / Clay
"Need better lineage"
Risk Team Lead
TBD via call recordings / Clay
Expansion champion · +30 seats
Trading Desk Lead
TBD · Future vector
Exploring real-time pipelines

Each node includes LinkedIn URL, email, phone, title, and any aligned usage data from Common Room. The AE can see at a glance who to reach, what they care about, and where we have product engagement.

Tasks

Tasks auto-populate into Salesforce from Outreach — this is where we set up sequences and steps. The AE works out of Outreach, and activity syncs back to the CRM automatically. More on the specific sequences in the next section.

PART 2C

Outreach Infrastructure

Outreach Sequences — Built in Clay, Pushed to Outreach

For each buying group, we draft targeted emails in Clay using the enriched account data and known signals, then push the completed emails into Outreach sequences. The AE works entirely out of Outreach — they review, personalize if needed, and send. Tasks from these sequences auto-sync back to Salesforce.

Sequence 1 — Champion Enablement

Field
Details
Target
Maria Santos (Lead Data Engineer)
Objective
Arm our champion to advocate for expansion internally. Provide her with ROI data and the expansion business case she can bring to leadership.
Why
She's the existing champion and our strongest internal relationship. We need her to open doors to the risk team lead, compliance officer, and VP of Technology.

Sequence 2 — Risk Team Expansion

Field
Details
Target
Risk Management Team Lead + key team members
Objective
Scope the +30 seat expansion. Understand their pipeline orchestration use case and get them into a demo or onboarding conversation.
Why
Their team has already requested to onboard — this is inbound demand, not a cold pitch. We're responding to their stated interest and making it easy to move forward.

Sequence 3 — Compliance / Lineage

Field
Details
Target
Compliance Officer
Objective
Turn their stated lineage need into a scheduled demo. Show how Dagster+ lineage and compliance reporting meets their requirements.
Why
They've already articulated the need ("better lineage") and Dagster+ has already passed their internal security audit — the objection removal is built in. This is a feature-led conversation.

Sequence 4 — Trading Desk (Future Vector)

Field
Details
Target
Trading Desk Lead + team
Objective
Plant the seed for a future expansion. Share how Dagster+ supports real-time orchestration and get on their radar as they explore options.
Why
They're exploring real-time pipelines — not urgent for this deal, but worth building the relationship now. Low-pressure, value-first introduction that sets up a future conversation.

The Flow

Clay
Draft emails using enriched data + signals
Outreach
Emails pushed into sequences
AE
Reviews, personalizes, sends from Outreach
Salesforce
Activity auto-syncs back to CRM

LinkedIn Connection Automation

In addition to email sequences, we'd set up automated LinkedIn connection requests to contacts across both the original team (to strengthen existing relationships) and the expansion teams (risk, compliance, trading desk). These would come from our Account Management or Customer Success teams — not the AE — so it feels like a natural extension of the existing relationship rather than a sales motion. This multi-threads the account across channels and surfaces additional intel from LinkedIn activity.

PART 2D

Ongoing Intelligence

Start with the AE

Before configuring anything, I'd sit down with the AE and understand what signals they actually care about most for this account. Every AE works differently — some want real-time alerts on everything, some want a weekly digest. The signal infrastructure should be built around how the AE wants to consume information, not how we want to deliver it.

That conversation would cover: What signals would change how you approach this account? Where do you prefer to see alerts — Slack, email, a doc? How often do you want updates? What's noise vs. what's actionable?

Signal Sources

Source
Tool
Signals Tracked
Why It Matters
Usage / Product Data
Common Room
New user sign-ups (especially from risk/compliance teams), usage spikes or drops, feature adoption (lineage, compliance reporting), support tickets
If risk team members start logging in before the deal closes, that's the strongest buying signal. Usage drops would flag risk.
Job Changes
Clay
Buying committee role changes, new hires into data/risk/compliance leadership, departures
If the VP of Technology leaves or a new CDO joins, the deal dynamics change immediately. Clay's ongoing enrichment catches this.
Funding & Company News
RSS.app
FinServe in the news — funding rounds, M&A, regulatory changes, earnings, leadership announcements
In financial services, regulatory news creates sudden new compliance needs. Funding or growth news validates expansion timing.

How Signals Get Delivered

These signal sources act as triggers that push information to wherever the AE works best. The delivery method is a conversation with the AE — here are the options:

The important thing is that signals are actionable and delivered where the AE already works. We'll configure the routing based on their preference and iterate as the deal progresses.

PART 2E

Handoff to the AE

What the AE Receives

The AE gets three things that let them work the account immediately:

1
Account Map / Org Chart — The visual map of all identified decision-makers and end-users across the original team and expansion teams. Each contact has: LinkedIn profile, email, phone number, job title, deal role, known need, and aligned usage data from Common Room. The AE can see at a glance who to reach, what they care about, and where we already have product engagement.
Key Artifact
2
Account Planning 1-Pager — An outline covering: account snapshot ($78K current → $136K target), the expansion opportunity and timeline (Q1 budget closing, contract expires Q2), prioritized signals, the buying committee and their known needs, and the recommended engagement sequence. Everything the AE needs to understand the account strategy without a voiceover.
Strategy Doc
3
Outreach Sequences — Ready in Outreach — Four email templates (one per buying group) are already built and pushed into Outreach. Tasks auto-populate to the CRM. The AE just opens Outreach, reviews the emails, personalizes where needed, and starts sending. They work entirely out of Outreach — everything syncs back to Salesforce.
Ready to Execute

The AE should go from receiving this handoff to sending first outreach within 30 minutes. The account map gives them the "who," the 1-pager gives them the "why and when," and the Outreach sequences give them the "how" — all pre-built and ready.

PART 3

Scalability

Scalable Account Launch Workflow

Everything in Part 2 was manual — research, CRM setup, email drafting, signal configuration. The one thing I'd build to make this repeatable is a Slack App that kicks off the entire flow, from account intake through to ready-to-send sequences in Outreach.

STEP 01

Slack App Trigger

AE fills out a Slack form: Account Name, Deal Type (Expansion / New Biz), Key Signal. Takes 2 minutes.

STEP 02

Clay — Find or Create

Form triggers a Clay workflow that first checks: do these contacts already exist in our CRM? If yes, pull existing data. If net-new, run People Search + waterfall enrichment (Apollo → ZoomInfo).

STEP 03

CRM Actions

Clay pushes enriched contacts into Salesforce. Expansion opportunity created from template. Contact Roles assigned based on deal-role tags. Custom fields populated.

STEP 04

Content Generation

Clay drafts personalized emails for each buying group using the enriched data and known signals.

STEP 05

Push to Outreach

Completed emails pushed into Outreach sequences. Tasks auto-sync to Salesforce. AE is notified — ready to review and send.

Slack (trigger) Clay (enrichment + content) Salesforce (CRM) Outreach (sequences) Apollo ZoomInfo

How We Ship It

We build out the full workflow — Slack form → Clay → Salesforce → Clay content generation → Outreach — and then QA test it heavily before rolling it out to the team. This means:

What this changes: The manual process from Part 2 (research, CRM setup, email drafting, sequence building) goes from 3-4 hours per account to a 2-minute Slack form submission + automated enrichment and content generation. The GTM Engineer's role shifts from doing the manual work to QA'ing the automated output, adding the strategic layer (account map, 1-pager), and iterating on the workflow as the team uses it.

Where This Goes Next

Once the Account Launch Workflow is running and 15-20 accounts have been activated through it, there's enough data to build the next layer: a proactive expansion signal scoring model. Instead of waiting for an AE to say "help me work this account," the system surfaces the best expansion candidates automatically — scored on seat utilization, new team mentions, feature requests, contract timeline, and health trajectory. A weekly ranked list of the top 5 expansion-ready accounts, delivered to the AE team in Slack. That shifts the GTM Engineer role from reactive to proactive.