Persistent discounting is almost never a sales problem. Buyers cannot evaluate a product in isolation. They always hold an implicit alternative in mind, and that alternative determines which of your attributes register as valuable. If you don't define the comparison set, buyers default to the most familiar adjacent option, which is usually the cheapest.
Choosing the frame where your genuine differentiator becomes the buying criterion is the highest-leverage marketing decision most companies make, and it costs a workshop at seed stage versus a rebrand plus sales retraining at Series B. The work is research, not brainstorm: interview won deals, ask what they'd use if you didn't exist, and find the attribute competitors couldn't truthfully claim.
The second decision is resourcing, and the honest answer depends on facts about you, not on what any agency sells. Below roughly $10k/month in media a specialist freelancer usually beats an agency. Once a channel is proven and needs daily operation, in-house is usually better value. We turn down about one inquiry in four on exactly these grounds.
What decides outcomes here
Choose the comparison deliberately
The frame where the thing you're best at decides the purchase. Everything else in messaging follows from that choice.
Positioning lives in the sales conversation
A repositioning that only reaches the website doesn't move win rates, because buyers meet the old frame the moment they speak to a rep.
Ask what an agency would tell you not to do
One that agrees with everything is selling. Willingness to disagree is the best available proxy for usefulness in month eight.
Own your accounts and assets from day one
Ad accounts, pixels, audiences, repositories, design files. If a supplier resists this, their retention strategy is friction, not results.