I would bootstrap as long as possible. As long as you're able to engage engineering resources for continual product enhancement; the customer support team to ensure customers are churn-proof happy; the marketing team to generate awareness, leads, and optimize the sales process; and the sales team to close business, keep going on your path. Where things get tricky is in terms of competition. If you're bootstrapped, it's harder to compete against a well-funded adversary (or adversaries) because they can do much more in terms of generating awareness. Their marketing team can attend many conferences. If your sales cycle is aided by in-person contact, conference and trade shows could be important. They are not cheap. Your marketing needs may also require a huge amount of demand generation. This can become really costly. (See the Fan Duel sports betting marketing campaign in Q3/4 2015. Mega expensive!). Depending on your product category, investment can also play a role in how prospective customers perceive you. If you're selling to the enterprise, having Blue Chip backing from Kleiner Perkins or Sequoia will impress those who look for this external validation. (You've surely heard of the “No one ever got fired for buying IBM” statement?). VC funding also helps with publicity, and media coverage if you care about that and need TechCrunch clips. There are many successful startups that never took any money. The vast majority or startups, in fact, don't. Based on your description above, though, it doesn't seem as if my thoughts apply to you. If you already have partnerships that are working for you, global customers you can leverage in those regions, a product that is clearly providing value to your customers, and you can fund growth from cash flow or other options (debt financing, perhaps), I'd keep to your path. The larger and more successful you become, the better the terms you can negotiate if and when you decide you can't live without outside investment.

I infer from your question that you haven't worked in a marketing leadership role before at a startup. "I handle ...sales." Are you Head of Sales, too? If you are, and you're actually capable of making a meaningful contribution to revenue generation, your value to the company and the two founders multiplies. The FAR MORE important issue is why you have waited so long and invested so much in this company without summing your role, expected contribution, quantitatve objectives and milestones, and already agreed on terms reflecting whatever this aggregate value is/will be. You've just invested 500+ hours of your life based on assumption and hope. I've personally been down your road before, and done what you did. It's not smart. The bottom line in startup life as an employee is that cash is better than equity. So few startups translate into anything that will improve the food or eat, or pay for your kids' education that you're far better off taking a cash/equity split as Alex Crutchfield suggested. If you're really the Head of Marketing and Sales, I'd ask for a high singe-digits equity stake (not options but with reverse vesting), with 50% in salary that you can spend to live. If you're rootless (no kids or a big financial nut every month), and are up for the adventure, you might be willing to accept less.

"Losing tens of thousands of dollars on sales and marketing." 1. Do you mean that you had a negative ROI from this branding/acquisition spend, or it failed to meet your expectations? In other words, you didn't see the sales return you expected. ie. you thought you'd see a CTR of 3.5% and it was only 1.75%. 2. Did you spend this money on consultants or other things like technology, lead databases, etc. and they clearly didn't deliver (meaning it was more clear fraud/failing to fulfill the contact then just not seeing the expected ROI)? Every company who has ever invested >$100K has "lost" tens of thousands of dollars as described in #1. It’s inevitable that some areas of your spend will be lower than others, but this “loss” perception can be due to faulty marketing spend attribution. (Attribution is way beyond this response). >>>>>First, I’d be happy to talk to you about filling this role. Alternately, this is what I'd do if you just wanted a demand generation person: 1. Research your target markets at the buyer level. What other services/technologies does this cohort purchase or has purchased in the last 1-5 years. (Purchase can mean subscribe if you're talking SaaS). 2. What are the top 4-5 vendors of these services? 3. Identify the ones that started their traction rise 4-5 years ago. 4. Go to LinkedIn and do a keyword search for those companies. Within the company results, use keywords like acquisition marketing, go to market, and demand generation to find former employees. 5. Create a list of those individuals. Eliminate those with titles below Manager. 6. See where they are now. If they're out freelancing, that's whom I'd contact first. What you're trying to do is find someone with recent domain experience who made a meaningful contribution (lead velocity from among your target audience) to his/her former employer. As I said, I’d be happy to talk with you about the bigger picture because demand gen is a subset of an integrated marketing and sales strategy. In particular, I would emphasize getting really granular with your awareness-conversion funnel, from confirming benefit-centric messaging and reviewing your landing page and site metrics, to your product trial experience and retention activities. I'm happy to talk with you about specifics.