Hiring Roadmap: Which Roles to Add at Each Revenue Milestone

A framework for product, ecommerce, or SaaS businesses, but logic applies to most small/mid-sized firms.

Stage 1: 0 to 250k - Prove There Is A Real Business

Goal: Find repeatable demand and a real margin while spending as little as possible on fixed headcount.

Typical headcount: 1 to 2 people, heavily founder led.

Non negotiable roles:

• Founder as Chief Everything Officer

  • Owns sales, delivery, product decisions, basic finance

  • Talks directly to customers, all the time

• Part time financial help (bookkeeper or accountant)

  • Monthly books

  • Basic cash and tax hygiene

Optional but useful:

• Virtual assistant or operations assistant (fractional)

  • Inbox and calendar

  • Simple admin, order processing, basic CRM hygiene

Contrarian angle at this stage:

Most advice tells you to "hire early" to free yourself up. That move is often just ego in disguise.

At this level, every full time hire eats a giant slice of your revenue. One salary at 80k inside a 200k business is 40 percent of revenue before you pay rent, stock, ads, or tax.

Guardrail:

• Keep payroll under 20 percent if you can

• Use contractors and fractional experts for design, dev, ads, and legal instead of full time hires

If you cannot sell and deliver yourself at this stage, hiring more people does not fix the problem. It just spreads the pain around.

Stage 2: 250k to 1 million - Get Out Of Pure Founder Chaos

Goal: Stop being the bottleneck, without turning into a meeting factory.

Typical headcount: 2 to 5 full time equivalents.

At this stage demand exists, but the founder is probably still approving every decision, answering every customer question, and doing sales at night while half asleep.

Core hires

1. Operations Coordinator or Generalist Operator

Call this person ops manager, project manager, ecommerce coordinator, whatever fits. The function matters more than the title.

They:

• Own order flow or project delivery

• Build basic checklists and standard operating procedures

• Chase suppliers and partners

• Keep tools and systems up to date

This is usually one of the highest leverage early hires, because it clears the founder's brain to focus on sales and product.

2. Customer Support or Account Manager

Dedicated customer contact shifts the tone from "founder answering DMs" to "actual business".

They:

• Handle inbound questions

• Track issues

• Protect reviews and retention

• Start building a library of customer language

3. Fractional finance brain

Not just bookkeeping. You need someone who can look at your numbers and tell you:

• True gross margin by product or service

• Ad spend and payroll as a percentage of revenue

• Basic forecast for cash over the next six to twelve months

This can be a part time controller or outsourced CFO type.

Common mistakes at 250k to 1 million

• Hiring a full time senior marketer before you truly know what channel works

• Hiring a full time CTO when a strong agency or senior freelancer would do

• Hiring "strategy" when the real constraint is process and delivery

Guardrails at this stage:

• Payroll under 25 percent of revenue is a solid target

• Revenue per employee moving toward 150k plus

The mental reframe:

At 250k to 1 million, you are not "building a team". You are buying back founder time in the few places that will grow revenue or fix obvious operational pain.

Stage 3: 1 to 3 million - Build Systems And Owners

Goal: Turn a founder led hustle into a machine that can run without you for a week.

Typical headcount: 5 to 15 full time equivalents.

Data from SaaS firms at 1 to 3 million annual recurring revenue shows median revenue per employee for bootstrapped companies around 100k, with funded firms often worse.

That is not something to copy. That is a warning.

Most small firms that hit a plateau here did one of two things:

• Hired too many senior generalists without clear ownership

• Hired lots of juniors without any real managers

Core owners you now need

1. Head of Operations

This is the person who wakes up thinking about:

• Delivery reliability

• Gross margin

• Capacity and staffing

• Process quality

They should gradually own:

• Supplier and vendor relationships

• Warehouse or service delivery workflows

• Basic reporting on on time delivery, error rates, and service costs

2. Revenue Owner

The label can be Head of Growth, Marketing Lead, or Revenue Lead.

Their job is simple to describe and hard to do:

• Owns lead generation, conversion, and repeat purchase or renewal

• Lives inside channel data

• Works tightly with ops to ensure the promises made in marketing can be kept

If you are founder heavy on sales, this role might start part time, focused on marketing and funnel, while you still close deals.

3. Stronger finance lead

You now need more than month end reconciliations.

This person:

• Builds a simple model that links revenue, cost of goods sold, payroll, and overhead

• Tracks payroll and ad spend as a percentage of revenue

• Flags when you are hiring ahead of cash

• Supports pricing decisions and basic scenario planning

This might still be fractional, but the level is higher.

4. People owner (often part time at first)

You do not need a full HR department, but you do need someone responsible for:

• Hiring process

• Basic performance management

• Onboarding

This can sit inside operations early on.

Supporting roles that often make sense now

• Channel specialists: performance marketer, email specialist, marketplace manager

• Senior customer success or account management for B2B or higher ticket B2C

• Product manager if you have a software or product roadmap that keeps slipping

Mistakes at 1 to 3 million

• Copying enterprise org charts

• Creating too many "lead" or "head of" titles with no real authority

• Letting revenue per employee fall under 150k while people brag about "growing the team"

Guardrails:

• Payroll trending inside 25 to 30 percent

• Revenue per employee aiming for 200k plus

• Clear ownership for revenue, operations, and finance

If you cannot write a one page document that shows, by name, who owns each piece of the customer journey, you are not ready for the next stage.

Stage 4: 3 to 10 million - Build A Real Leadership Layer

Goal: Replace founder heroics with a leadership team that can handle growth and shocks.

Typical headcount: 15 to 50 full time equivalents, depending on sector and product mix.

Growth from 3 to 10 million is almost the opposite game compared with getting to the first million. For many B2B SaaS founders, the sales and marketing team that got them to 3 million cannot run the playbook needed for 10 million.

The same pattern shows up in ecommerce and services.

Core leadership seats

By now you should have, in some form:

1. A true Head of Operations or COO type

• Owns supply chain, production, delivery, or service operations

• Drives margin improvement projects

• Owns service level agreements and customer experience quality

2. A Head of Revenue or CMO type

• Owns the full revenue number, across new and existing customers

• Manages channel leaders

• Works closely with product and operations

3. A Head of Finance

• Owns the forecast and cash plan

• Supports funding moves or bank relationship

• Runs board level reporting

4. People and Culture lead

Title aside, this person is responsible for:

• Hiring, onboarding, and retention

• Manager training

• Helping remove poor fits fast, instead of letting culture rot

Supporting structure

Under that layer you will see pods:

• Growth and performance team

• Product and merchandising or product management

• Customer operations or customer success

• Tech and data

The contrarian point here:

The job is not to keep adding roles. The job is to increase the quality of the leadership seats and reduce the number of direct reports per leader to something sane.

Typical failure modes:

• Founder keeps too many reports and becomes a blocker

• Leaders are hired but have no real decision rights

• Payroll drifts above 30 percent while everyone complains about "overwork"

Guardrails:

• Revenue per employee above 200k for most online first companies

• Payroll held near the planned band, with clear tradeoffs when it shifts

• Leaders who know their numbers weekly, not just monthly

If a leader cannot tell you their three core metrics and how they are trending, you do not have a leader. You have an expensive contributor.

Stage 5: 10 million plus - Professionalise Without Killing The Edge

Goal: Build a company that can handle bigger bets, more scrutiny, and more risk, without smothering what made it work.

At this point, your hiring roadmap gets more specific to sector, but a few patterns hold.

New seats that usually become relevant

• Chief level roles with clear scope: CEO, COO, CFO, CMO, CPO or similar

• Data and analytics lead that supports all functions

• Legal and risk support, internal or external

The main challenge here is not "who to hire". It is "what problem are we solving by hiring this person".

Questions to ask before adding any senior role:

• What function is clearly breaking as we grow

• What decisions are consistently late or poor

• What metrics are flat or declining that a leader could improve

Tie each senior hire to a specific measurable shift.

Guardrails remain the same:

• Payroll within a healthy percentage band for your sector

• Revenue per employee not trending down year after year

• Clear accountability for profit, not just revenue